Older Woman Pt. 01 - Squirt

I was new in town in my late 20s. The city was familiar, I had lived there a few years before, but I didn't know many people. I went to one of those coffee shop singles groups organized online to meet new people. It would be nice to get out and meet new friends, and if finding a new friend for play happened, all the better.

She was in her early 40s, over 10 years older than me at the time, with long blonde hair, blue eyes, and full, motherly hips and breasts that gave her a mature, curvy plumpness. She had a nice smile, but dressed more like she should be at home doing puzzles than out with a bunch of single people looking to meet. She wasn't the prettiest in the group, or the sexiest, but she was giving off an energy that she was open to whatever was going on, so I was drawn to her.

I sat toward her end of the table and began my assessment. We made solid occasional eye contact, and she was talking with those around her about her quiet life now that her kids weren't living with her, and getting adjusted to a new city. As it turned out, she was from a state where I had spent a couple of years, so I made a couple of little inside jokes about that area to give her a little taste of home. This got her attention, and by the end of the evening we were sitting next to each other talking about her hometown and why she moved away. We exchanged instant message names (pre-Facebook, life has changed so much) and spent the next couple of nights flirting away. By the time Friday came and she asked me over to watch a movie, it was obvious more than a movie was on our minds.

She lived alone in a tidy one bedroom apartment in a quiet little complex on the south end of town. The apartment was meticulously clean as she showed me around, which made the cord hanging over her headboard in her bedroom seem all the more out of place. I traced the cord down to a vibrating massager sitting next to one of the pillows on her queen sized bed. She saw me notice the cord, and at first went flush with embarrassment, then smiled and said that it was her little friend. I chuckled and told her every woman should have one or a few, and we went back to the living room to watch the movie.

To say the movie itself was boring would be an understatement. We had a couple of beers while the bedroom door loomed open, the foot of her bed with the vibrator an ever looming presence in my mind as we sat on her couch in front of the tv. I thought about her being over a decade older than me, with kids already grown, yet her sexuality still running free. My mind became curious with ideas of what she would be like in bed, how she would masturbate with the vibrator, and what would be her desires and cravings from a man. I knew from chatting with her that she obviously enjoyed men, but it had been a while. She had also mentioned she had decided not to have any more kids after her second child, so she had her tubes cut afterward. The alcohol made my thoughts wander, and I decided it was time to do something about it.

Did I say the movie was boring? By an hour in, I wasn't paying any attention to it, embroiled in the thoughts of this older woman that had officially become a true MILF, a mom I most definitely wanted to fuck. I don't know for sure what she was experiencing, but I had a feeling she was going through a similar experience about me, wondering what I would be like with her, waiting for a move that may or may not come. In the end, it didn't take all that much. The movie was bad, the beer was buzzing, and sitting next to her, I casually placed my hand on an ever so slightly provocative spot on her thigh just a little up from her knee and gave a gentle squeeze. She made a very small, almost inaudible gasp, and then reciprocated by slightly opening up her thigh toward me. We exchanged looks, and I went in for a kiss without hesitation, knowing she was ready and willing for me.

We made out on her couch like teenagers. Our hands moved and caressed over each other's bodies exploring new feelings and textures. She was soft and smelled like flowers. With me on top, her hips opened, and my covered erection pressed up between her thighs, which gave the moment all new energy as she rocked her hips up to greet me. My cock was pulsing, knocking at her door, and her body wanted to answer.

"Do you want to move this in there?" I asked, nodding my head toward her bedroom door.

"I do, but I'm a little nervous," she replied. "I don't want you to think I do this all the time, ask younger men to come over."

"I don't think that, if you had men over all the time, why would your little friend be hanging over the headboard?"

She smiled, and I got up and led her from the couch to her bed.

"There is one thing I need to do before we get started", and she got a large towel from her bathroom, pulled back the blankets on her bed, and spread the towel across the mid-section of her bed.

I puzzlingly asked "what's that for?"

She said "I get quite a bit wet... you'll see. That doesn't bother you does it?"

Now I had been with women that got a bit wet, or so I thought at the time. I once had a car that notoriously had the outline of an ex-girlfriend's pussy on the passenger seat (gross, but honestly, it was such a perfectly shaped stain my perverted ass never bothered to fix it, and it was hard to see). I had seen girls squirt in porn, but I knew enough to know that just didn't happen in the real world, and what was in porn was most likely urine anyway. Seeing how clean she kept the rest of the apartment though, putting down a towel for a little spillage fit in line with what I knew of her, so no big deal.

After putting the towel down, she stripped, almost clinically, folding her clothes and placing them on what I presumed to be "her" side of the bed. I had been around the block enough to know my queue, so I hastily removed my own clothes, and attempted to match her own organization by placing them nicely on the opposing side of the bed she was now getting into. I joined her under the sheets and we picked up again making out, this time with our naked bodies pressing against each other, her soft plumpness pressing and squeezing up against me.

Her hand expertly traced its way to my cock, where she examined it with her fingers to learn its size and shape like a blind person learns a face. I let out a small groan as she began to stroke it, and she eased me to my back, my ass on top of the towel.

"Lie still" she commanded, as she straddled over top of me. At this point, I still hadn't felt her pussy, although I was wishing I had done more. She seemed in such eagerness to move on to sex that I had no idea how wet she was, or if she was turned on at all. This was quickly answered as she crouched over me and guided the tip of my cock through the lips of her dripping wet pussy. What I felt as she lowered herself onto my dick wasn't so much a tight, slippery friction, but a very wet, slippery glide, like rubbing your dick in two silk pillows covered in warm oil. I'm not a small guy, but even as she fully enveloped my cock down to the balls, I could feel it move around in her while it pulsated with plenty of room to spare. With the squishy, loose grip on my dick, she began to rock back and forth, her breasts pendulously swinging in my face, massaging her clitoris into my crotch. She breathed heavily with her rocking, moving herself with a low intensity that built over the next few minutes.

I was enjoying myself thoroughly as she used my body to bring herself to climax. Her pussy felt like none other I had experienced, a wet gentle caress in a firm, hard world. As she got closer to orgasm, I began to notice my balls felt a little different, and we were making sloshing sounds as we moved. I began to think the towel may have been a necessity after all.

She climaxed with a high moan, pushing me in as deeply as possible. Suddenly, I felt a rush of warmth all over my balls, hips, and upper thighs as she literally came all over me. She collapsed against me with an exhausted sigh.