My name is Jordan, and I was 17 at the time of this story. The Kaplans used to be my next door neighbors. We lived in an older neighborhood situated in a suburb of a midwest city. Unfortunately, the Kaplans had to move away because John (Mr.) Kaplan was diagnosed with testicular cancer. It probably didn't help that they lived underneath high tension wires. Either way, they moved to a different neighborhood farther west in the same town.

My family and I did not necessarily stay very close to the Kaplans, but we kept in contact with them. The Kaplans, Marcy and John, had two young boys named Josh and Max. Right before they moved, both of their children were still to young to speak. During my junior year in high school, Josh and Max had grown up to the terrible ages of 5 and 7.

The Kaplans were a pretty mobile couple, and now that their children were old enough, they enjoyed going out a couple of nights a week. Being a teenage boy that they trusted (and who desperately needed money), Marcy asked me if I would babysit for her two sons. Babysitting really wasn't my thing, but because I knew them, I agreed to do it.

It was a Wednesday or Thursday night during July. I was dropped off at the Kaplan residence by my father at around 7pm. John and Marcy were frantically running around, trying to get ready. It's not that I had never noticed Marcy's figure before… I just never really considered a 41 year old woman to be attractive. Tonight, however, Marcy was wearing a silky green dress that ended just above her knees. Her short, red hair was done up on top of her head and held in with many bobby pins. The dress revealed a pretty inviting and sizeable cleavage that I had never noticed before. She was a small woman, only about five feet tall, and I had never expected her breasts to be as large as they were. She was only slightly overweight, pretty average for a middle aged woman. Marcy and John gave me the basics about the night- they were going to a party, should be back by ten, put the kids to bed by eight, yadda yadda.

"When should I tell my dad to pick me up?" I asked them, innocently enough.

"Oh, don't worry about that. I'll drive you home" was the reply that Marcy gave me. Being the horny 17 year old that I was, my mind immediately flooded with fantasies involving Marcy.

Finally, the Kaplans left for their party in their sleek BMW 700 series luxury sedan. I spent the next hour playing board games and video games with Max and Josh, nothing too special. I let the kids stay up until nine after making them promise me that they wouldn't tell their parents… big mistake. The kids were so excited to stay up that they tore ass all over the house, throwing whatever they could get their hands on. One of the items that they DID get their hands on was one of Marcy's bras. It was dark green, the same color as her dress, and Josh was running around with it on his head. Just the sight of Marcy's bra was enough to get me excited, so I sent the kids to bed right away. I cleaned up after them, picking up the bra last. I ventured into Marcy and John's room and found the dresser in the corner. The top drawer contained Marcy's bras and panties, and I had a quick look through them as I put the bra back. Goddamn it, I was so horny that I had to go into the bathroom and rub one out right then. My cock is only about 6 inches in length, but it's pretty thick. I'd say that it's proportional to my size- 6'1" with a husky build, black hair and hazel eyes. My erection was so hard that it almost hurt!

Around 10:15pm, Marcy and John returned home. They asked me how everything was, and I basically told them most of what happened that night (with some obvious exceptions). John thanked me and paid me forty dollars, a nominal sum for such an easy night. Marcy had gone upstairs to change into shoes that were more comfortable and came back downstairs about five minutes later. Then, it was time to get my ride home.

I got into the passenger seat and noticed that Marcy was still wearing the same dress. She crossed around the front of the car on her way to the driver's seat. My eyes were practically pasted to her chest and midsection the entire time. I let out a little moan, thinking about how great it would be to fuck her. The green, silky material of her dress danced around with the slight breeze that Marcy created as she walked around the car. For a split second, I could see the outline of the bottom of her breasts all the way down to her thighs. Even though I had jerked off less than a half an hour before, my cock started to swell again in my pants! I stirred a little bit in the passenger seat, trying to re-adjust and hide my growing erection before Marcy got into the car. It didn't help that I checked her out thoroughly as she bent down to get into the driver's seat.

"All set?" Marcy asked me.

"Yeah, I'm ready" I replied as I faked a yawn. Marcy started the car and told me that I could put on any radio station that I wanted. We backed out of the garage and started on the 15 minute drive to my parents' home.

"So, what's new with you since we moved away?" Marcy inquired.

"Oh, not much. I'm still working at Piggly Wiggly (grocery store) and dating Michelle," I said.

"Oh really? Is that the same girl that we met right before we moved?" Marcy asked with interest.

"Yeah, it's the same girl."

"How long have you two been dating now?" Marcy continued interrogating.

"We've been dating for almost two years now," I dutifully responded. I switched through the radio stations, trying to distract myself a little bit. Meanwhile, I kept looking over at Marcy's chest nonchalantly as she focused on the road. I was starting to get anxious and uneasy.

"She's in the grade below you, right?" Marcy prodded.

"Yeah, she's a sophomore," I stated as I fidgeted again.

"Well, you'd better be careful, then!" Marcy chuckled in response.

I hesitated a little bit and replied, "what do you mean?" I knew exactly what she meant.

"Well, Jordan, being teenagers that you both are, I'm sure that your relationship will get physical at some point if it hasn't already. You just have to be sure that you're ready for whatever you're doing and that you're taking the proper precautions. On top of that, you need to think about the legal consequences that could possibly be involved." It seemed like Marcy was giving me a lecture. I didn't particularly enjoy this because she was starting to sound like my mother.

Without thinking I responded "well, it shouldn't matter because we're both underage. Technically I would have to be 18 or older for it to be rape." I didn't realize it until after I said it, but I just flat out admitted to Marcy that my girlfriend and I had been having sex.

"I see" Marcy said with a wry smile on her face. She then looked over at me at the precise moment that I had been looking at her chest. Embarassed, I looked away and faked a cough, pretending that I didn't notice her as she caught my sneek peeks. "So, do you use condoms when you two have sex?" Marcy asked with a whopper of a question.

I stalled, "do we really need to talk about this?" I asked her, becoming quite visibly uneasy.

"Well, do you talk to your parents about it?" Marcy asked.

"Hell no! They'd cut my dick off!" I quickly replied.

"Well, you can talk to me about it if you want to. I won't tell your parents. It's important that you can ask questions if you have any. I'm not trying to scold you for having sex- teens will have sex either way- I'm just trying to help you if you have any questions," Marcy reassured me.

"Okay" I said, still uneasy. "Well, yeah, we use- I mean I use condoms" I reluctantly offered. My eyes continued to nervously dart all over the place. Time and time again, my gaze landed upon Marcy's chest or thighs, and she caught me staring again. I don't know how many times she caught me looking at her, but it must have been at least a half dozen times.

"That's good- at least you're being careful" was Marcy's reply. "So, am I to assume that you've never fucked a girl without a condom before?" she prodded. I didn't even notice, but our conversation was getting dirtier and dirtier. I just kept answering, trying not to let on that I was checking her out, all the while failing to conceal my boner.

"No, never. I wouldn't want to take the risk. I'm not worried about STDs because we were both virgins, but I don't know what I'd do if I got Michelle pregnant. She wanted to try it without condoms once, but I didn't want to" I recalled.

"You didn't want to?! Weren't you curious about how it feels?" Marcy asked in disbelief.

"Well, YEAH, but it feels good enough with a condom, you know?" I said as I again stared at her body. Of course, she caught me starting at her again.

she yelped. I nearly jumped out of my seat.

I said sheepishly as I turned and looked out the window. The car was silent for a few moments as she continued driving. The road cut through several farmfields on the way to my house. I didn't know what to say or do, so I just remained silent and my boner started to subside. All of a sudden, Marcy turned down a dead-end road that ended in a neighborhood that was being constructed. "Where are we going?" I asked her, seriously confused. She didn't answer at first. I was genuinely stumped. We approached the turnaround circle at the dead end. It was pitch black as not even street lights were installed yet, which made sense because none of the houses were completed. The only light coming from the overcast night was from the dashboard and the headlights. Marcy whipped around the circle and parked the car facing outward. She turned off the headlights, but left the car running. "Marcy, what's going on?" I asked her.

"Jordan, come on! I've been talking to you about sex for the past 8 minutes, repeatedly catching you staring at my tits and body. All the while you've been trying to hide your boner, practically wetting your pants with a combination of precum and drool from your mouth. Now John has testicular cancer, you know that. Sex isn't exactly pleasurable for him right now, which means that it is non-existant for me. I'm on birth control pills so that I don't get any unwanted pregnancies, but a whole lot of good that does when I can't even get fucked. Now, you have a couple of options…" Marcy paused to catch her breath. The whole while I was petrified, practically shoved against the passenger door of the car as she yelled at me.

"Your first option- tell me 'Marcy, I'd like to go home' and I'll drive you home and we'll pretend that this never happened." She waited for me to reply, but I did not. Though scared of what I might hear, I wanted to know what my other option was. "Your second option-" she continued, "is you can lift up this dress of mine and fuck me without a condom because I'm fucking hornier than I have ever been and I'm one step away from pinning you down and raping the hell out of you!"

I couldn't believe what I had just heard. My mouth was agape, but I couldn't say anything at all. I just sat there and stared at her in disbelief. A few seconds passed before Marcy said "that's what I thought. Now recline your chair as far back as it can go." I slowly but surely obeyed her command. Reclining the seat in a BMW 700 series creates quite a bit of room in the front of the car. I just sat there, my boner practically tearing through my pants.

Marcy gingerly raised her body off of her seat and seeminly floated over to my side of the car. I was practically laying down because the seat was so far reclined. She slowly, carefully lowered herself down onto me so that she was straddling me. My hands were still at my sides because I didn't know what to do at all. "You can touch me, you know," Marcy reassured me as she grabbed my hands and gently placed them on her chest. To my surprise, she was not wearing a bra at all! Her nipples were very hard by this time, and her breasts were shockingly full for a small woman such as herself. My girlfriend was at least 5 inches taller than marcy, but her breasts were nowhere near as big. Marcy had to be a healthy C-cup in size.

I began to gently squeeze her breasts, almost massaging them through her dress. Marcy must have been enjoying this because she started to moan and she was grinding her crotch against mine in a slow, deliberate motion. She was so wet that I could feel her moisture through my pants! I was on the verge of coming right then, but Marcy slowed down and started undoing my belt. "You don't mind, do you?" she asked me as she unzipped my pants. I still couldn't talk, so I just shook my head 'no'. I was praying that she wasn't going to give me a blowjob because there really wasn't room and I wouldn't have been able to last more than a few seconds.

Her small hands swam through the opening in my boxers and fished out my raging erection. Upon discovering the girth of my cock, she let out a pleased I was still fondling her breasts in symmetrical, circular motions with my hands. Once she had my cock out, she lifted her dress so that it was bunched up around her hips. This was the first glance that I got of her string-bikini style panties that were the same color and material as the dress. I looked at the area around her pussy and her panties were absolutely soaking! Marcy resumed grinding her pussy against my cock, only this time I could definitely feel the warmth and moisture of her pussy. Her cunt was so wet and warm that it felt like a big tongue rubbing up and down on my shaft. I continued to rub her breats when she leaned forward and practically shoved her tongue down my throat as she let out a moan that shook both of our bodies.

Personally, frech kissing somebody has always been a huge turn-on for me. Here I had Marcy, writhing on my lap, shoving her tongue into my mouth and moaning while her wet pussy lubed up my cock through her panties. I was so overwhelmed with pleasure that I was shaking. Marcy was able to pull her lips away from mine just long enough to say in short bursts "okay… just… okay… now take… take my panties off… right now… and fuck me! FUCK ME!" I lifted her off of me with one arm and pulled her panties off with the other. Because the way we were situated was kind of awkward, I was only able to pull her panties off one leg at a time. I was too impatient to pull them all the way off, so they just sat there, wrapped around her left knee when I lowered her back down onto me. She grabbed my cock and started swirling the head around the lips of her pussy, making my cock dripping wet with her juice. This felt so warm and so good…

Marcy raised herself above me and lined my cock up for insertion. Here it comes, I though, here it comes… But she didn't completely sit down on my cock- she only let about a half inch of the head slide inbetween her soft, warm, slippery lips. She did this several times, teasing me unbearably until I couldn't take it anymore. After what seemed like ages of my not being able to speak, I abruptly said "holy fuck Marcy, holy fuck. I need to be inside of you right now. I want to come deep inside of you."

"That's all I needed to hear" she replied. Marcy lined my cock up with her pussy and slowly sat down on it. Now, I'd fucked my girlfriend's 16 year old pussy more times that I could count on two hands, and I've gotten countless blowjobs, but nothing could have prepared me for this. Yes, two children probably made Marcy's pussy looser than it used to be, but it didn't fucking matter at all. Without a condom, just Marcy's sitting on my cock was like getting a hummer from a girl with a really warm, really wet mouth that had a million tongues in it. I almost filled Marcy up with cum before I was even all the way in her.

As she was finally sitting on my cock with all of her weight, I had to lean my head back as I said "oh my fucking god, that feels so damn good." Once my cock couldn't go any deeper into her pussy, she started rocking back and forth without lifting up and down. My girlfriend does this all the time, but with a condom on, it doesn't really do anything for me. Without a condom, the head of my dick was moving all around in the back of Marcy's pussy, and it shot bolts of pleasure through my body. After only about a minute of this, Marcy was screaming, presumably having an orgasm. I didn't know what was going on because I was concentrating too much on not blowing my load that early.

After her first orgasm, her pussy was even wetter than before. She started to lift her body off of my cock, her pussy practically sucking on my dick like a lollipop as she slowly moved up and down. I was groaning audibly, something that I usually never did with my girlfriend. I put my hands on the sides of Marcy's ass and ferociously grabbed her buttcheeks. I loved pulling her cheeks apart and pushing them together as my cock slid in and out of her pussy. Marcy leaned forward and once again starting shoving her tongue into my mouth. I knew that I wouldn't be able to last long from there. Lifting her body up by the butt, I began thrusting my pelvis up, jamming my cock into her pussy as hard as I could. Marcy started moaning again in unison with my thrusts. Her moans were muffled by my mouth, which was plastered all over hers. My hands started moving up her back and the thrusting of my pelvis lifted Marcy up so that she was bouncing on my crotch as I thrusted upward. I was now fucking her deeper than I had ever fucked my girlfriend, and Marcy was letting out seemingly demonic moans of pleasure. My hands made it up to her shoulders, and I began to pull down on her shoulders so that I was fucking her even harder than before. With one hand pulling her onto my thrusting cock, I moved my other hand to the back of her head and pushed my mouth onto hers so that we were almost violently kissing.

About two dozen thrusts later in this position and I was exploding. Marcy seemed to be coming at exactly the same time that I was coming. I came harder and longer than I had ever come before. Wave after wave of pleasure shocked through my body as I could feel my come absolutely soaking the inside of Marcy's pussy. I was screaming with pleasure, so loud that my vocal chords hurt. Marcy was screaming right back, but our mouths were still plastered together, so our screams were muffled. After what seemed like a dozen shockwaves, I was finally done coming. I let go of my grip that I had on Marcy, but she just collapsed on top of me anyway. After a few minutes, my dick started going limp and it came out of her pussy with a Along with my dick came what seemed to be gallons of my come, pouring out of her pussy. We made a fucking mess out of that nice BMW's front seat, but I didn't fucking care. I came so hard that it seemed like somebody punched me right in the gut.

Marcy thanked me and we got back on our way to my house. She tried to give me more money "for taking care of her sons", but I told her that I should be the one giving her money! We left it at that, and after she dropped me off in my driveway, I never spoke to her again.

story by: B_1

Tags: fantasy cheating male / older female older female / males sex story

Author: B_1

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