Hollywood's Hot Cougars 04: Gabrielle

February 2013

I'd never had sex with a black woman before.

That probably shouldn't have been right on my mind as I went into the backseat of Gabrielle Union's car. But it was a little less overwhelming than other topics.

Like the fact that I had been running into a famous, sexy actress at Miami clubs for the last few weeks in the first place. Or the fact she'd actually talked to me in them. Or the fact she confided in me about her recent separation with Heat superstar Dwayne Wade - one that actually wouldn't last. But neither myself nor her knew that at the time.

And then there was the newly discovered fact that she wanted to start getting over him. With the furthest thing from him. A.k.a., me.

Someone who was 13 years younger than the 40-year-old Union, someone who wasn't a basketball player or athlete - unlike Wade and fellow ex Jason Kidd - and someone who was white. That was the complete opposite of Dwayne Wade, all right.

Maybe I was merely someone who met those checkmarks. Maybe the fact I did, and she'd actually talked to me these last few weeks, made her less patient to find someone else. Maybe heartache was making her think less than straight, although she really hadn't shown much anger or tears. Not in front of me, anyway.

I didn't know if she just thought of this idea, or planned it all along. If she'd been testing me all along, that was one thing. If she had no plans or expectations to get this far with me until now...that opened a whole new can of worms.

The responsible thing to do would be to stop and sort that out. And get a better sense of just how separated Gabrielle and Dwayne really were. There were multiple ways this could come back to bite me in in the ass - in the bad way - if the wrong moves were made at the wrong time.

Instead, what outweighed that was the mere fact she wanted to take me to her place. And that this was the culmination of weeks of talking, suspected flirting and actual flirting. And the shallower fact that this was a famous, stunning celebrity who wanted to do this with little old me.

And at the last minute, as we got to her car at the back of the club, I added the rationalization that I'd never been with a black woman before.

That was the last one I needed before I got into her backseat - and Gabrielle put hers on my lap once she got in with me.

"Now?" I asked, trying to think of anything other than the feel of her ass against my crotch. It was a battle I couldn't win, though. "I thought we were...leaving first."

"It's been a while for me. I gotta be picky," Gabrielle started. "I didn't figure this out lightly, you know. So I should at least have a taste before I drive you anywhere." After a pause, she added, "Maybe you need one too."

I didn't really need that much to make up my mind. With Gabrielle in my lap, wearing a light grey dress with a fair amount of cleavage, and with the fact it wouldn't take much to roll her dress up, I could decide then and there. But if she thought I needed more to go on...

Which included leaning in and kissing me, apparently.

While Gabrielle already had her legs around me and lips on me, I only took till now to touch her and kiss her back. The second I felt her body and felt her lips moving back against mine, I knew I'd waited too long. No sense holding back now, though.

Nevertheless, we just stayed there and kissed, hot and bothered but content for the moment. Until Gabrielle started to move her hips, gliding her full, round ass against my obvious bulge. I pulled back to catch my breath, then exhaled heavily again when she moved her ass on me again.

She gave me one of her big, million dollar smiles, but there was a naughty tinge to it. At that point, my hands went up from her back and feeling her dress, to brushing her neck and actually feeling her luscious bare skin.

Between the bare feel of that and the feel of her clothed ass on my cock, I was still barely breathing. The least I could do is return the favor, though.

I had Gabrielle arch her hips up, so I could roll up her dress enough to put my left hand under it when she came back down. I could feel that she did have underwear on, but my fingers had no trouble moving the front of it to the side. As I started doing that, I rested my face against her neck, no longer contest with feeling her skin.

The second I kissed her neck, I knew I wouldn't take my mouth, lips or tongue off of her for a long time. If ever. Or maybe I'd wait until my finger was done down below. It was making progress brushing her wet pussy and clit, which Gabrielle further proved by moaning and starting to move her ass around again.

Soon enough, she rolled her ass up and down my groin as my finger started pumping her, and I kept kissing, licking and suckling every inch of her that my mouth could reach. Indeed, I didn't take my entire mouth off her for longer than a second.

For some reason, I had enough memory left to remember one of Gabrielle's comments at that moment. Fueled by that, I finally pulled my face from her, pulled my finger out of her, and put my wet finger in my mouth - getting the taste of her she suggested I needed.

Yeah, she got it right again. "All right, there's my taste," I said out loud in case she didn't get it. But she did anyway.

After I licked my lips of her. Gabrielle put her lips back on mine again. Her ass resumed riding me, and this time, my hands were ready to meet it. I lifted the back of her dress, placed my hands on the back of her panties, yet quickly slid them over to the thick, heart shaped flesh underneath.

I pulled my lips back, needing to exhale again. Gabrielle smiled, more teasingly than wide this time. She put her hips up again, which I took as a cue to slide the back of her panties completely down. With her legs still around me, I couldn't take them off, but they weren't covering the juicy parts anymore.

I let myself put both hands on her naked, glorious behind for a few moments, but I did need to take one of them away. So I did, letting my left hand go back over to her pussy, fingering it anew while my right hand stayed on her ass.

With that, Gabrielle resumed bucking herself against my finger and rolling her ass over my clothed, throbbing cock. Between that and cupping her smooth, gorgeous behind, I was barely holding it together.

Then I had the bright idea of actually thrusting my hips and groin against her. She then had the bright idea to lower her dress straps. My next bright idea was to take my hands up and lower the top of her dress, revealing her braless, full breasts and mouth wateringly hard, chocolate nipples.

My hands returned to her pussy and ass as my mouth latched onto her breasts, barely keeping myself from completely biting her nips. I settled for suckling them and her boobs while she rode me and arched against me harder and faster than ever.

"Oh God, that's it. Taste me, fuck me..." Gabrielle started saying. "You wanna cum in your pants, I won't stop you..." That almost made two of us. "Then you'll have to go somewhere to dry them off and take them off...won't you?"

The logic was almost airtight. Not to the extent that her pussy was tightening on my finger, but close.

In response, I wiggled my finger inside her, squeezed a perfect cheek from behind, and deeply sucked on a perfect nipple in front. Gabrielle just kept riding my lap, rubbing herself on my finger and on top of my cock. She even held my face as I kissed in between her tits.

Finally, she lifted it up to kiss me, slide her tongue into my mouth, and then take it out and glide it over my cheek. Her wet, full lips and mouth started kissing and rubbing my face and neck as much as mine had on her. It was all too much.

When Gabrielle went to my ear, rubbed her lips over the lobe and suckled it down, my finger went out of control. So did my other hand as it palmed her ass, tempted to start spanking it. However, she groaned right into my ear and started cumming before that.

Not too long later, so did I. Right in my pants.

Gabrielle's wetness started coating my left index finger, while my own went all over the inside of my underwear and my thighs. I would have been more embarrassed, if not for everything other than me cumming in my pants. Even when that fully registered, I remembered her practically giving me the green light.

In fact, she seemed to encourage it. There was too much sexy evidence to suggest otherwise. Indeed, I would really need to go home and wash my underwear and pants. And Gabrielle's home was closer than mine.

Now I got it. She tested me out, gave me an actual legitimate, urgent excuse to go to her house - and it seemed like she had ideas on how to pass the time there. Ideas that involved more than fingers, and more clothes coming off.

Currently, my top idea was to get my finger out of her, which Gabrielle quickly kissed and licked before kissing and licking my lips. She shot me another big smile after that, unwrapped her legs around me, and sorted herself back to normal. Once her panties and dress were back where they were, she got herself out of the backseat and got up front to drive.

I stayed in the back, not particularly fit to walk just yet. Besides, walking around at the moment, with what was going on in my pants, wasn't something I wanted to hurry up. At least things would start to get drier by the time we got to her house.

Indeed, I was in somewhat better shape to walk out when we arrived at Gabrielle's. I adjusted to walking with damp underpants - remembering Gabrielle was probably doing the same thing. It gave me an odd sense of equality as we made our way inside her house.

After taking a bit of a tour, Gabrielle brought me to her laundry room. Getting the hint, and feeling myself more ready for what might happen next, I started removing my pants and everything underneath them.

When I threw them in the washer, put detergent inside and turned it on, there was nothing left to distract me from Gabrielle seeing my cock for the first time. The noise was somewhat bothersome, but we could ignore that. I hoped that I was somewhat distracting to her, anyway - and I stood a better chance now that I wasn't as flaccid.

"Sit up," was all Gabrielle said. Trusting her judgment, I sat on the vibrating washer and managed to keep myself from sounding weird. But the sounds I made when Gabrielle put her hand on my growing cock were harder to contain.

It got worse when Gabrielle bent her head down to start kissing and tonguing my cock. I threw my head back, then looked down to truly take it in. Her lush lips slid over the underside of my head, her dark hair almost tickled my thighs, and her utterly gorgeous face looked so peaceful and at ease with my cock inside of it.

I threw my shirt off, feeling hotter with it on now. Completely naked, I placed my hand into her hair and held on - not too hard, of course - as Gabrielle's sultry lips, hot mouth, smooth tongue and soft moans surrounded my cock.

She sucked it down extra hard before slowly coming off, then stood straight up, to my initial disappointment. But like I did moments earlier, she paused to get the last bit of clothing off of her. Once her dress fell to the floor, she stepped out and bent back down to suckle me, now completely naked too.

This gave me an actual look at her incredible ass, bent over and in the air. I wanted to reach over for another few squeezes, but I wasn't in the right position. I just settled for putting my hands in her hair, then onto her face, savoring the pure silk of her facial cheeks, the pure silk of her mouth surrounding mine, and the pure sight of my light hand on her darker face.

Gabrielle looked up with her deep eyes, bobbed lower on me a few more times as my thumb stroked her cheek, then popped off once again. "Okay...I need to sit down now," she declared, standing straight up again.

She motioned for me to get off the washer - which I barely remembered I was sitting on at this rate, regardless of the vibration. But I remembered enough to get off, leading to Gabrielle taking my place. Now she was sitting on the washer, savoring how it moved around below her, and parting her legs open in the meantime.

It was my turn to bend down and put my head between someone's legs. It was my turn to thoroughly lick someone and devour them. Although I'd already tasted Gabrielle, doing it right from the source was worth the slight discomfort of bending down in this position.

Gabrielle's moans, gyrating crotch, and the feel of holding her naked hips were added bonuses. After a while, my hands went up to cup her breasts and tweak her nipples again. Indulging in that while wiggling my tongue around inside her was almost too much right there.

Perhaps I needed to hurry this along in more ways than one. But I still stayed down there for an extra minute, in case Gabrielle needed more time to savor this position. However, it probably took about 40 seconds until she said, "I need more than your tongue now..."

I could have given her my fingers in response, and I did let my thumb stroke her opening for a moment. But instead of pushing it in, I stated, "Then stand up and turn around."

I stood up straight, making sure my back was okay as Gabrielle got up from the washer. She turned herself around, put her hands on the washer and pressed her hips against it, moaning anew from the vibrations. All I needed to moan was the sight of her bare, shapely ass sticking out in front of me, though.

I had just wanted to get behind her and start fucking. But before I knew it, I was right on my knees behind her instead. And despite my earlier plans to bypass using my fingers, I started using them anyway while my mouth glided up her right leg.

Yet again, I wasn't going to take my mouth off her for a moment. Especially not once I got to...the area above her legs. I could have kept my mouth on there for a long time - to the point where it'd probably wind up right in the middle eventually. But I was still smart to know that would be ill-advised.

Not wanting to delay the inevitable any further, I got on my feet and took my fingers out, leaving Gabrielle ready to accept my cock. Yet as I grabbed it and brought it towards her pussy, I thought of one last reason to hold off.

Instead of putting myself in her pussy, I leaned my shaft right up against the crack of her ass. Immediately, it looked like one of the best decisions of my life, among other things.

"You like that, huh?" Gabrielle spoke up. There were technically words to answer that, but none were coming to mind. So I settled for grabbing hold of her ass, pushing both cheeks against my shaft and thrusting between them. At that point, she turned her head around.

"Oh...now I see it," she moaned. God, why didn't I do this before? There must have been others...like her in my social circle over the years that I could have...

No. It ended up here, so it all worked out. And judging by how Gabrielle was pressing herself against the washer, letting its vibrations work on her as I worked on her ass, it was working for her too.

God, I could cum right now and it'd be okay. Shoot all that cum all over that ass, that body...I'd have enough for one more after that, right?

Best not to take chances, though.

I indulged in just a few more thrusts, and in rubbing her cheeks against me just a little longer. But finally, I took my cock out from between her crack, and put it right into her pussy at long last. By then, it slid right in.

"Oh, fuck..." Gabrielle said it for me. She said it again when she leaned her hands on the washer, bent down a bit further and backed her ass up. I said it even louder when I pulled out and thrust back in, seeing her jiggle as a result.

I got louder still when my hands left her hips and reached around to her breasts, taking her nipples as I started pumping faster. I tweaked her breasts and dropped my lips to her shoulder, kissing her there as if she needed any more stimulation. As if what I was already doing wasn't pushing her close - or so I hoped.

When I rested my chin on her shoulder and she turned her head, however, it sure looked promising.

Gabrielle burned a hole in my eyes as I felt her grind herself against me. Yet when she went in to kiss me, it was nice and slow although we were going faster down below. Inspired, I gently took her bottom lip into my mouth and suckled it down, trying my best not to bite it - not too hard.

We managed to kiss sensually for a while, yet Gabrielle quickly slid her tongue deeper into my mouth before long. I did the same to her the next time out, then we both opened up and let our tongues dance together. All the while, I kept fucking her and rubbing her nipples along.

When we broke off, I kept looking at her while my right hand left her chest and went down to her pussy. It rubbed her along as I kept fucking, not breaking any eye contact with Gabrielle. Once I rubbed her enough to get my finger wet, I brought it back to her nipple and rubbed it along.

"Oh, shit, motherfucker..." Gabrielle called me, throwing her head back. In response, I brought my left hand down to rub her, then brought it up when I could get her other nipple wet with herself.

Gabrielle just pushed back harder and faster, losing herself and tipping me over too. I took my head off her shoulder and stood straight, content again to watch her back and ass move around. There was only so much more movement I could stand, though.

"I'm gonna cum in something else again soon..." I warned.

"Take it out...I wanna see it this time..." Gabrielle gasped. "Make us both cum with those fingers...shoot that hot white cum all over me..." It'd be a tall order - at least one part of it might - but I could give it a shot.

Pulling out before I lived to regret it, I immediately put my left hand between Gabrielle's legs and put my right hand on my cock. I started fingering her right away, giving her a fighting chance to cum first. But as soon as I started tugging while watching her trying to cum, almost no head start would be enough.

I settled on holding out for 20 seconds before I started jerking myself too. Gabrielle turned her head, tightening herself around my two left fingers while my five right fingers pleasured myself. But all the pleasure really came from seeing Gabrielle.

It also came from playing back those last words in my head. Thinking of shooting myself and how it would look on her...on that ass...and how she'd see it and apparently get turned on too...

Like she clearly was right now while fucking my fingers and watching my cock...

I practically squeezed her pussy and my cock at the same time. Nevertheless, it was clear I was gonna give out first. I could only try to aim my cock at her ass, and it was a direct hit.

I tried my best to aim the next few spurts at her upper back. I also made sure Gabrielle was watching too. I also saw she was still moving herself around, but not enough to make me miss.

Yet it was enough for her to tighten around me harder. I regained enough brain power to wiggle my fingers around too. Between that and seeing my cum on her, it appeared to be the clincher.

I started catching my breath just as Gabrielle started cumming on my hand. This time, she couldn't keep her head turned, throwing it back as she gave out. I kept an eye on her for the both of us, though - especially since I didn't want my cum dripping off her and onto her floor.

It was still in place by the time I pulled my wet fingers out of her. At that point, Gabrielle turned back to me, then reached her hand back to grab my arm. Doing the best she could in her position, she made me drop my wet hand on her - and on top of my cum.

I was briefly grossed out from touching my own cum, until I remembered how this part started. Besides, I had to catch my own a few times when tissues weren't available.