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.
With my cock as hard as it can be while still constrained in my pants, she reaches back and down, grabbing my cock over my pants, squeezing it, and stroking it, holding it out as if to try to slide it into her body. I brush her hair to the side, and kiss her neck and ear, then whisper into her ear, "You're such a horny little girl. Don't you wanna take your time?", as I push her hand away.
I reach one hand up her back, to the back of her head, where I grab a handful of hair and gently, but firmly pull on it, tilting her head back. With her neck fully exposed, I kiss and bite on her neck and shoulders, as my other hand slides up and back down her panties, getting right over her pussy. Right over her clit.
I start rubbing her clit with my finger, then sliding my hand further down, I take one finger and slide it in - not too deep. Then a second finger - a little deeper. Then a third - deeper. All the way. Standing there. Fully clothed. Watching ourselves... watching her in the mirror. As I finger fuck her. Holding her from behind. Nice and deep. Getting her right up to the edge.
I then forcefully turn her around, facing me, as I hold her close to my body, and walk us to the bedroom, just next door. I put her back to the bed and push her down onto it. With her legs hanging off the edge, I get between her legs and look down at her. She knows what's coming and is ready for it. I reach my hands down, grabbing her legs, and as I lift them up, I lower myself down.
First gently, lovingly kissing her legs. Caressing and kissing her calves, and the back side of her knees, up, along the inside of her thighs. I slide my hand up, under her dress, up to her pussy, where I begin to rub her pussy and clit, still with her panties on. She moves her hands to either side of her pussy, clenching her legs as she slightly lifts up her dress, exposing her panties. Obviously, that sets me off.
I reach my hands up, pushing her dress further up, over her stomach as I quickly move my face past her pussy, stopping for a second on her clit, and sucking on it, still with her panties on, then farther up, where I begin to kiss her waist and hips and stomach. Then, with an intoxicated tenderness, I move back down, finding the top of her panties with my teeth, clenching them, and pulling them down as far as I can. Of course, the curves of her body -- her hips, her ass -- prevent me from pulling her panties all the way down, but I get them down far enough down where her perfectly kept pubic hair peeks just above the top.
I quickly move to getting her panties completely off, reaching my hands up on either side of her body and pulling. I want to maintain the sensuality of the moment, but I also don't have any interest in letting that slow me down. I pull hard, forcing her to adjust her body to help me get them past her ass and hips. Once free, I quickly pull them completely off, sliding them past her heels, which she still has on.
I again take her legs, holding onto them, kissing them, as I move up her legs. This time keeping my eyes up on hers. My hands reach up, between her thighs, up to her pussy, where I use my thumbs to spread her lips, finding her clit and slowly working it over. Of course she's already hard, so I begin to work it over harder and harder. When I finally get my face right up to her pussy, and hold there for a minute so I can just look at and admire her pussy as I play with it with my fingers. Then slowly moving my mouth over onto her clit, I tease it with my tongue, increasingly replacing the fingers with my tongue.
As I take over her clit with my tongue, I slide my hand over her pussy, teasing her. I spread her lips, pushing just the tip of my finger into her pussy, up and down the length of it. She loves that and wants more. I hear her moan, as she reaches her hands down, onto the back of my head, gently holding and pushing me into her.
As she does, I begin to push my finger into her pussy. She is so wet, so loose, it easily slides in, but I know she wants more. I take a second finger and slide it in, twisting it as I do. I bend and reach my fingers up against the top of her vagina, fucking her pussy with my fingers. Then a third finger. Deeper. All the way. I feel her arching her back in pleasure, and pushing her body down, against my hand, trying to get my fingers deeper into her pussy.
I begin to fuck her harder, and faster, and deeper, and she begins to get louder, and wetter, and looser. She grabs my hair, hard, and pushes my face into her pussy even harder as she grinds and fucks my face until she starts to cum. Jesus I love when she cums. It gets me so hard and excited.
After she cums a second time, she tries to pull me up, but I don't let her. I want more. I keep myself down between her legs. Now with even more passion and more force, I suck on and lick her clit, fingering her deeper and harder. I try to slip a fourth finger in while she cums a third time. And fourth. And fifth. And only then do I relent and let her pull me up to her face, where I jokingly ask her, "Was that OK?"
She's out of breath, but responds, "Shut the fuck up and just fuck me."
Without using our hands, we slide and grind up against each other, until the head of my cock finds her pussy and I slowly push it in. "God, you're so fucking wet," I say to her as we look into each other's eyes. "You're such a horny little bitch. How many times did you cum?"
"Four? Five?!?! I haven't even cum once." I tell her, as I begin to thrust my cock into her pussy with slow, long, deep movements. "I'm going to take my time, and enjoy this - your pussy." I extend both my arms straight out, pushing my body up and off of hers, so that the only things that are touching is my cock and her pussy. We fuck like this for a short minute because it feels too good, but I can't hold back from going harder, and deeper, and faster.
I slide my hands under her shoulders, wrapping her tightly in my arms and against my body. She lifts her legs up and around my waist pulling me down into her. I open my mouth and sensually bite down on her neck and shoulder as I fuck her, harder and faster, but more deliberately now. With purpose. I feel her wet pussy wrapped around my cock, until I begin to cum deep inside her, thrusting into her, until she has every drop of my cum.
I lay there for a minute to catch my breath and come down from the high and exhilaration of having just fucked the hottest, sexiest woman on earth.
She then begins to laugh and gently push me off of her, telling me to let the dogs out, as I roll off her and back into the soft bed.