NOT Your Grandma's Book of Progressive Erotica: Vol 3

Keep Up

Every young man dreams of that older woman who will show him the ropes, allowing him to learn a thing or two before returning to the wild for a girl around his age. What they don't realize, is that it can become very demanding if you stick around too long. I stuck around for a couple of months with the milf I hooked online – rather, she hooked me.

I was checking emails while on lunch break at work. There was one notifying me of a message from the dating site I was somewhat active on, so I decided to check it since I rarely received them. The woman was ten years older than me at the age of thirty-five. I had never been approached by an older woman before, especially one that had kids and was just looking to get back into the dating scene.

When I read her message, I knew she probably didn't want to date, so I was certain that she wasn't being entirely truthful to me.

After our first date at a comedy club, I drove her back to her car, where we hugged and parted ways for the night. She texted me the following day thanking me for such a great time and being a gentleman. From what she had told me after the show at the bar, a lot of guys she had met were dirtbags and I was the first nice guy she had met. Brownie points were nice, but since she was so much older than me, I saw her more as a potential friend than anything.

The second date was at her place because her kids were at their dad's place for the weekend. She cooked such a delicious meal that I knew it would be hard to say no to any of her future requests. After dinner, we went to the living room and watched a movie on her couch. She snuggled right into me for the entire length of the movie. When it was over, I checked what time it was and suggested that I should get going.

"Are you sure you can't stay for just a bit longer?"

Grabbing my hand, she led me to her bedroom and I figured I could spare another thirty minutes, or so. She took me right to her bed, pushing me onto it and straddling me with our clothes still on. As she kissed me, she undid my belt and zipper, pulling my cock out and jerking it until it was rock hard. Once that occurred, she then had me move to the middle of the bed and then began to suck my cock.

Her mouth felt so good on it that I felt like I should have been the one cooking the amazing meal beforehand. The way her tongue slopped around my cock and made it wet, twisting and twirling, was unlike any of the younger girls I had dated. I was sure to make note of what she was doing in case I had to teach my next girlfriend how to please me the right way.

When she stopped sucking my dick, I pulled off my shirt and so did she. Then she got off the bed, quickly took off her bra and pants and then joined me back on the bed to pull my jeans off for me. She straddled me while she kissed me quickly and then began to grind against my cock a bit.

My cock was half out of my boxer briefs at that point and just waiting for her pussy. She pulled them off and then started sucking me off again. I saw her right hand reach down into her lace panties and knew she was fingering herself. For a thirty-five year old woman, I couldn't even tell that she had kids. Her body was so round and perfect that I couldn't believe I had been so lucky.

She soon stopped sucking me again, leaned back to pull down her panties and then lifted each leg to take them completely off. Straddling me once more, she then rubbed my cock on her shaved pussy for a bit and slid it inside of her.

Her pussy felt just as good as any other one that I had had before. The big difference was the way she moved on top of me and made it feel so intense that I wasn't sure if I would last much longer than five minutes with her. I played with her boobs for a bit, licking and sucking on her nipples, then put my hands on her waist as she began to show me how a real woman would ravage her man.

Moving so quickly on my cock ended up being a good thing. Because it was so wet and so quick, I actually felt like it was becoming less intense for me and so I was able to control my breathing more. When she stopped her intense ride to switch positions, she was soaked and so was I. We switched to doggy and as soon as I was inside of her, she was pushing herself back into me as if I couldn't go deep enough. I held onto her waist once more for dear life as she nearly knocked me over with her round ass.

Many violent thrusts later, she came again, so I smacked her ass quite hard.

"Ou," she moaned playfully. "You should pull my hair too."

I listened and then began to fuck her as hard as I could. She began to moan loudly and I didn't stop until she had cum again.

"Finish me in missionary," she panted, turning over and lifting her legs out to the side.

Entering into her pussy again, I realized I was getting quite winded, so I'd have to pace myself so she could get off one last time before I did. I slowly fucked her pussy, slamming my cock all the way in and then slowly pulling backward. She was gasping for air every time I went fully in and when she wrapped her legs around me at one point to start kissing me, I knew she was close to cumming.

"Give me your best shot," she whispered into my ear as I then adjusted to fuck the shit out of her.

Like a jackhammer, I bombarded her pussy with my cock. The slapping sound of my balls against her were pussy were in such tight intervals that there was barely any time for breathing. She moaned loudly and then I felt her gush all over my cock. Instantly I began to cum as well, filling her soaking wet pussy up with my cum. When I finally slowed down and stopped, we were both out of breath.

"Well that was fun," she said with a great big smile.

I smiled back and then pulled out of her pussy to reveal the creampie that was waiting to pour out.

"Mmm," she moaned, as she fingered herself and then put all the cum into her mouth.

I was quite impressed with how much she enjoyed my cock and my cum. Girls I had met before could be kinky and act like sex fiends once in a while, but this woman seemed like she loved it all.

"So do you think you could handle more of this?" she asked.

"Why wouldn't I?"

"This was just a beginner's test, the real one will come soon enough. So are you sure?"

I looked down at her sexy body and knew that I couldn't say no. I'd prove I could do it one way or another, even if I had to beg for a second attempt.

"If you're willing to give me the challenge, I'm more than willing to complete it. I never back down."