I had been single for the past 3 years or so after what I thought was a serious relationship ended rather abruptly. In high school and my early 20s I was relatively reserved around girls. I didn't want to be perceived as a typical horndog and thought girls deserved respect. As I went through college and my 20s, I began to shed that mentality.
Around this time, internet dating was in its infancy, but I figured I'd at least give it a try. To my surprise, I was actually fairly comfortable with the format, but some of the women online were hesitant and indecisive. And even though I was interested in a substantial-type relationship, I was also interested in something for tonight, so I kind of made it a point to raise the potential (and the desire) to have some sexual encounter, if not on the first date, sometime shortly after.
After a few months, and a few dates, I came across this one woman. She was in her 40s, athletic, and local. I contacted her, and we started chatting and exchanging emails, and within a week or so, we were setting up our first meet-up.
It was clear our real intentions and expectations were just to find a hook-up. I was looking for a sexy older woman who would indulge my sexual desires. She was looking for a young hot guy whom she could explore her fantasies with.
On our first date we just went to a restaurant and ended up taking a short romantic walk around a nearby park. As the date was coming to an end, I walked her to her car where, as we went to hug good-bye, I quickly turned her body to mine, and I leaned in and gave her a gentle, but passionate kiss, which totally surprised her, but also sent a tingle down her body (she told me later). She hadn't been handled and kissed like that in years.
From there, we began to develop a more serious relationship. At first, she might have been a little embarrassed given our age difference, but I was totally excited. I would brag about and show her off to my friends. And, over time, as she introduced me to her friends, she realized they had no issues with, and in fact were a little jealous of, her and our relationship.
We nearly right away started having sex, and for me, it was amazing. For her, she loved having a cute, strong, young guy taking control of her body. Picking her up. Pinning her back against the wall. Forcing myself on her. I loved having a super sexy, independent, successful woman whose sexual motivations and inclinations matched mine. While she was seemingly indulging my fantasies, they were really fulfilling hers.
Now, a year or so into dating, we have a pretty mutually acceptable relationship. We totally enjoy each other. We are best friends. But also, we have our own lives. She works and runs her own company. I'm finishing up my undergrad. But in the end, we always find time to be with each other.
Tonight, I invited her to a gala/fundraiser for an organization where I do some work. Typically, when we go out, I'm going with her -- to one of her events, so tonight is unique, and I could tell she gave it special attention with what she was wearing. A tight, black and silver sequined dress. Slightly plunging, showing a little cleavage, ¾ sleeve, and cut just below mid-thigh; and black, open-toed high heels that have a little bit of a sparkle, but not stripper trashy, just sparkle. She looks amazing. I am kind of in disbelief that she is with me.
I'm in a slim-fitting dark grey suit, white shirt and solid-colored pastel purple tie.
At the gala, we have a few drinks, and while sitting at the dinner table we flirt and tease each other under the table or when standing by each other. Nothing over the top or obvious. I can tell everyone who meets her is totally impressed. Some of the women seem kind of jealous or intentionally dismissive, while most of the men are "friendly" and "engaging".
When the event is coming to an end, we go to the valet and wait for our car. As we do, we continue to subtly press our bodies up against each other, now maybe a little less coy about it. Once in the car, on the way home, she reaches her hand onto my thigh, and while she doesn't reach for my cock, the way she touches me has me totally turned on. Just a gentle, passionate caressing of my thigh. But only until we left the parking lot, but then, for the entire ride home, while we talk about various things, the only thing on my mind is making love to her. And I call it love, because it was never just sex, and it wasn't just fucking her.
When we get home, I try to play cool, like tonight was just another night. But that lasts until we step from the garage, into the house. I hardly let the door shut behind us before I grab her by her arm, pull and turn her back to me, quickly sliding my hand onto her back and up to the back of her head, where I grab a handful of her hair, tugging on it firmly, slightly pulling her head back as I tell her, "you are so fucking beautiful. I've been craving you all night."
She smiles at me and says, "Good. What're you gonna do about it?"
"Don't worry. We'll figure that out when we need to, but for now, I just want to kiss you." Before she can smile back or say anything else, I lean in and begin to kiss her. She, without any hesitation, kisses me back. But, as is often the case, and what I love, she kisses me with some dispassion, letting me, and wanting me to use my sexual aggression. I go along at first, as I slowly turn our bodies, and push her back to the wall.
As we continue to kiss, I can't hold myself back. I slide my hand up the front of her body, taking and squeezing her tits as my hand moves over her dress. Then further up, to her neck where I hold her there by her throat. I stop kissing her so we can take a second to look at each other. Without saying a word, and just through the expression on her face she tells me, "Do what you want to do to me. I need it."
I smile at her, then quickly spin her around, holding her tightly with her back up against my body as I stand behind her. We're now both facing the same direction and toward a large mirror. She looks at the mirror, watching the two of us, while I go right back after her body. I brush her hair to the side again, as I lean in and begin to kiss her neck and shoulder. I look up and watch her through the mirror, and watch me touching her.
I slide my other hand across her waist, feeling the shape of her body, as I move over her dress, down past her waist, below her dress, and back up, under her dress, between her legs, up to her pussy over her panties, where I hold her there. Her dress lifts so she can see my hand in the mirror, pressed up against her pussy. At first, she just lets me kiss and hold her, enjoying the moment, but then, as I pull our bodies closer together, she feels my hard cock poking her ass from under my pants. She loves that feeling and slowly begins to rock, and grind her ass back into my cock, at the same time, her pussy and clit begin to rub up against my hand.
