I really should have said this when I first posted this, but this short story is definitely NSFW. Proceed at your own risk.
I am in the process of figuring out how to make this short story its own book, which involves a significant expansion of the story. But this way you get to see one of my stories evolve.
Enjoy, and wish us all luck!
In high school we all thought Bob’s mom was the MILF in our group. She was always polite to all of us, bringing us snacks when we went over to their place. Sweet as could be, and as innocently hot as hell!
Bob’s dad never seemed to be around much, except every other weekend, but we got along well with him. He really seemed attentive to Bob, relishing in his accomplishments. Like when Bob won the 100 meter dash at the track meet. He always talked about Bob when we were around.
But he didn’t seem to notice that Bob’s mom was around most of the time. I think most of the guys respected Bob’s dad enough not to see it.
When Bob’s dad was around, his mom seemed to kind of disappear into the kitchen. I went looking for her once, and found her fixing dip and chips for us. I asked her if she needed any help, and she thanked me and sent me with the tray back into the other room before coming back out with hot dogs and sodas for all of us.
I brought a bunch of the dishes back to the kitchen to her while the other guys watched baseball with Bob’s dad. I helped her clean up for a while before saying, “well, there you go, uh…Bob’s mom.”
“It’s Jennifer,” she corrected me. “And I would say you’ve earned dessert. Would you like some cookies and MILF?”
She said it so quickly that I wasn’t sure I heard her correctly, and when she held a milk carton up, I was pretty sure I had gotten it wrong.
“Sure,” I replied, and she got out some freshly baked cookies and milk for me to enjoy for a few minutes before joining the others.
But I started to notice her paying more attention to me over the rest of the school year, and once she whispered it into my ear while the other guys were talking, “do you want some cookies and MILF?” before offering cookies and milk to all of us.
Before the end of that senior year, Bob’s dad suggested we all go on a week-long backpacking trip to celebrate graduation. It sounded like fun, so I went along with the planning. At least, at first.
A couple of weeks before graduation, we were all sitting around Bob’s kitchen table after school, planning on what to take. Bob’s mom, Jennifer, set down a plate of cookies for us, and a pitcher of milk right in front of me, and whispered “cookies and MILF?” in my ear. It wasn’t easy hiding my erection for the rest of the afternoon, especially when Jennifer was around.
After I got home that day, I started thinking about how Jennifer would be by herself while we were gone. It quickly dawned on me that I didn’t really have to go, did I?
I broke it to my friends the next day that I couldn’t go on the backpacking trip because my parents wanted me to go to the big family reunion that just came up. Of course, my parents didn’t know about it, so all I had to do was keep my friends away from my place for a few weeks while I packed for my “backpacking trip”.
When the day finally came, I drove over to the mall to hang out for a few hours to wait for Bob, his dad, and our friends to leave. I drove over to Bob’s around 9:00 AM.
Getting out of the car and walking up to their front door was harder than I thought. What if I misread Jennifer? Maybe she thought she was having fun harmlessly flirting with me, and had no intention of going further.
I knocked on the door, and Jennifer answered, wearing a robe.
“Oh, hello Jason,” she said. “Getting ready for your…reunion?”
“Oh, yeah, that got cancelled today,” I lied.
“I’m sorry to hear that,” she said, not really sounding all that sorry, and letting me into the house, closing the door behind me. “I guess that just leaves you here, without company?”
“Yeah, pretty much,” I admitted.
“Are you going to spend the week with your girlfriend?” Jennifer asked me carefully.
“Well, I don’t actually have one…yet,” I confided.
“Oh, that’s too bad,” she said, setting out a plate of cookies and pouring a glass of milk in front of me, letting her robe fall open a bit. “Would you like some cookies and …MILF?” she asked, letting her robe fall a bit more open, just enough that I could start to make out her nipples.
I looked her in the eyes as I took the glass from her, and said: “Absolutely!” and drank it down.
She smiled at me and let her robe fall completely open. “I was about to take a shower. Could you help scrub my back?”
It took me a second to process what she said, and I quickly answered “Oh, yes!”
She smiled at me, and led me by the hand upstairs to the master bathroom. I ignored how uncomfortable my pants were getting until Jennifer undid them and let them fall to the floor. “Now that’s…nice,” she said, holding my cock and giving it a couple of tugs. She smiled at me, and asked, “Do you have to go home this week?”
“Uh, no ma’am,” I stuttered as she let her robe fall to the floor.
“Good,” she said bending over as she turned on the water. She looked me in the eye and placed my hand on her breast, saying “I can be your girlfriend the week, if you want.”
“Uh, yes…yes, ma’am!” I stammered out.
“Call me Jennifer, at least this week,” she laughed as she stepped into the hot water.
“Yes, Jennifer,” I said as I watched, stunned, as the water ran off of her.
“Are you going to join me?” she asked, inviting me in.
“Yeah!” I said, scrambling into the large shower.
She was obviously having fun running her hands over both of us, giving me the soap and showing me how to soap up her tits and gently play with her under the spray of hot water for the first time. I didn’t really know what to do, but I was enjoying fingering her slick pussy in the hot water, and she had her eyes closed while I was doing it, moaning quietly and spreading her legs to let me play with her more.
She moaned loudly with her eyes screwed shut, and when she opened them, she smiled at me. “I think it’s time I gave you a late 18th birthday present,” she said.
“It’s only a few weeks… ” I barely managed to say before she kissed me deeply, and sank down on her knees in front of me. I was going to tell her she wasn’t that late, that my birthday was only a couple of weeks earlier, but really, it didn’t matter. I knew what she was going to do, but I still wasn’t prepared for it.
She slowly gave my clock a couple of tugs as the hot water cascaded over us, looking right at my cock. I don’t think I’d ever been so hard before in my life. She looked up at me and said: “you have a beautiful cock!”
“Thanks!” I replied just before she leaned forward to take it into her mouth.
She swallowed my cock like a professional, right to the root. She bobbed up and down on the shaft, humming, licking the head, lightly biting, while fondling my balls. She seemed to literally love giving me head, like sucking cock was what she was meant to do. I have no idea how she managed to keep me from blasting my life savings down her throat in the first ten seconds, but she kept going for at least a couple of minutes before taking my load and swallowing all of it right down.
She came up, still holding my cock, looking as proud as possible that she had given me my first blow job ever, that she was the first woman to ever make me cum in her mouth.
Putting my hands on her hips to hold her steady, she leaned back and rinsed her hair and mouth out. She held my cock as I watched the water streaming down her tits, off her nipples. I didn’t hold myself back and sucked in one of her nipples without warning, and she started laughing and playfully trying to fight me off. She quickly switched to holding my head to her breasts and moaning quietly again for a few minutes before pulling my face to hers to kiss me deeply. She curled up tightly in my arms in the hot water, and opened her legs to put my clock between them.
I thought that was it, we were finally going to fuck, but instead of putting me inside, she placed my hard shaft across her opening, and started to move her hips to rub her clit over my cock. She kissed me messily, moaning, and lustily moving against me until she broke the kiss, and breathing heavily, turned off the water.
“Lets take this to the bed, okay?” she asked, smiling.
“Sure!” I replied, unsteady from what we had been doing already, but absolutely ready for more.
She handed me a towel, and we quickly dried off a bit, just enough not to drip all over the floor, before she ran toward the bed, giggling, with me right behind her. We both jumped onto her bed, still damp, the steam from the shower billowing into her room. She kissed me hard, and held my cock, making sure I was still hard. She didn’t have to worry about that at all.
She used her hands to direct me on top, between her spread legs, and she spread her wet pussy lips wide for me and let me watch her rub the head of my cock all over her clit before putting it right at her opening. She looked into my eyes and nodded to let me know I should start to push into her. I felt a bit of resistance at first, so I pushed again and I popped into her a little, and stopped when I heard her gasp. She nodded again, and I started to slowly push in and out, slowly going deeper each time, listening to her moan as I went deeper. I was getting impatient, and pushed deeper, faster, with each thrust. However, when I finally pushed all the way in, she gave out a deep, guttural groan, and her eyes rolled back into her head as she arched her back, wrapping her legs around me, holding me tight.
I’d thought that I had hurt her by going too deep. “Are you alright?” I asked, worried.
“Oh, oh yes, I’m alright! Everything is wonderful! I’ve never felt anything like that! You’re so deep inside!” she said, and she grabbed my head to kiss me lustily. I was surprised to feel her pussy gripping my cock, clamping down on me, milking me, and she started to grind against me, making little grunting noises. “Fuck me, just fuck me already!” she growled in my ear.
That was all I needed to hear, and I started to ram my cock into her as she growled, yipped, moaned, and laughed lustily as she met my every thrust, milking my cock hungrily with her pussy muscles.
I can’t say I had any real technique, I was just learning how to fuck, but Jennifer was clearly enjoying what I was doing to her. With her, really. I was starting to figure out what each movement of her body meant, and I was eager to deliver what she needed. I could tell when she wanted me to slow down, and when she wanted me to really pound her. After shooting my first load down her throat in the shower, I was going to be able to hold off for a while, and keep fucking her the way she seemed to want me to.
Bob’s mom was an athletic and really enthusiastic fuck, not that I had any experience to contrast her with. Even on her back with me on top, she was very much an active participant to our fucking. She would have her legs clamped behind my back, arching her back and fucking her hips at me, almost as if she were trying to throw me off, even though that was the last thing either of us wanted. She seemed to be enjoying having me deep inside her as much as I was.
She started to moan loudly and really fuck me back, and I could feel my balls start to tighten up and my cum well up inside as her pussy started to pulsate and milk me, and I started to thrust into her as hard as I could. She began to start wailing, and holding me as tight against her as she could, and I yelled out as I pushed as deep into her as I could and I started to gush my cum deep into her, shot after shot as her pussy happily milked it from me.
We came down together, and when I really got a good look at her, I realized we were both still wet, but I was pretty sure it was from the sweat from our athletic fucking. Jennifer was smiling and making contented mewing sounds as she ground her hips at me.
“Wzz…was that as good for you as it was for me?” she croaked. “Aah, that was good!”
“Rr..Are you kidding? That was fantastic…BbJjenniiifer?”
“Were you about to call me ‘Bob’s mom’ again?” she asked, laughing.
“What? No! I just…”
“Admit it!” she said, throwing me around a bit with her legs wrapped around my hips, not letting me go.
“Good enough for now,” she said as she let go her grip on me. “But we have a lot to teach you this week!”
“Like?” I asked.
“While I try to tame that massive beast of a cock you have there,” she said, wiping up our cum dripping from her pussy, “we’ll have time to teach you that you can call a woman by her first name after you’ve fucked her good and hard!”