Gabrielle, Guest Star

October 19, 2010  |  dirty stories

It is always different to fuck somebody new. New skin, new lips, new way she kisses, new way she writhes, new way she comes. I don’t keep a lot of assumptions the first time. I don’t expect us to get off, I don’t expect to be able to tell when she comes, if she does. I don’t expect dirty talk, I don’t expect a lot of communication about what’s what. Of course I do my best at all of those things—but with someone new, you just never know. Maybe it’s the chivalrous service top in me, but I watch for cues and tend to take them from her, as best as I can.

Which is how I ended up stroking my cock, still wearing my tee shirt, my back up against the wall in my room, watching Kristen get fisted. By someone else.

After watching her get seduced.

Kristen and I had both noticed Gabrielle when we met her at a queer event a month or so before, so when she was in town this time, we made sure to make plans to meet up for a drink. Who knows what will happen, I told myself. Kristen told me she thought Gabrielle was pretty, and slutty and smutty and loud-mouthed enough to be that big river of energy that Kristen often seeks in those close to her. Gabrielle was running late. No ETA exactly. When we went off to meet her, I was a little bit skeptical about whether she’d even show. “I half expect to get stood up,” I sort of joked.

It wasn’t that I didn’t want to see Gabrielle. When I thought about it later, I realized it was because I had no part in setting up this date. Kristen and Gabrielle arranged it, and though Kristen texted me to ask where we should meet up (the dyke bar in Brooklyn, of course), I had almost no part in the asking, the saying yes, the gauging of how interested or not Gabrielle might be.

All night, I had trouble reading Gabrielle. I was interested, and curious about her—she’s a smart, hot femme who it seems can make anybody laugh. Her style is cute and chic. She’s short, a little shorter than Kristen even, who is 5’2″, and not thin but not so heavy, just enough that I want to grip the flesh on her thighs. She talks a lot, and says interesting things about all sorts of things—being poly, education, being an artist. I liked her immediately when we met.

But I couldn’t tell what was going to happen. I couldn’t quite get a grasp on the conversation; I sometimes felt like the third wheel. I’d bring the conversation around to sex, but it didn’t take long for Kristen and Gabrielle to start talking about other things, like the socio-economic makeup of the cities in which they lived, or the queer community friend politics.

I didn’t try too hard. The conversation was interesting, I jumped in occasionally. Mostly, it was fun to watch them banter back and forth.

Kristen had just made a pie, so we had a good excuse to take Gabrielle back to our place for a slice of it. They talked more. It was getting late. Finally, they started kissing, making out, on the couch. Gabrielle pushed Kristen down and worked her hand between Kristen’s legs, Kristen grasped at her back and shoulders and came once, twice.

“Can I take this off of you?” Kristen asked her, pulling at Gabrielle’s dress.

“Somewhere darker,” she answered. And we went into the bedroom.

They continued playing on the bed. Stripped off their clothes. I wasn’t exactly sure of my move … should I join? That would feel a little bit like forcing myself into the situation. Plus, I was really enjoying watching. I am usually so much closer to Kristen when she gets aroused, watching her skin flush while my hands are already on her body, and watching someone else do it was interesting, both puzzling and a thrill. They were adorible together, both eager, passionate in their kissing and handfulls of thigh and ass and tits.

I tried to be casual as I got out my favorite cock, slid off my jeans, still watching them kissing, touching, fucking, on the bed. I stood against the wall, one hand on my cock, and watched as Kristen lay back on the pillows, one hand gripping the bars of the black headboard as she opened her thighs and pushed against Gabrielle’s hand, inside of her as Gabrielle knelt between her knees.

I moved to sit on the edge of the bed up near the headboard, next to Kristen. Gabrielle’s whole hand was inside of her, disappearing at the wrist. I reached for the lube and offered it to Gabrielle. She noticed my cock, ready, and laughed. Kristen noticed it too, and reached for it with her hands, stroking it while I lowered my mouth and kissed her. We managed a whispery check in: “You okay?” “So great,” and she told me she wanted my cock in her mouth.

Gabrielle pulled out and Kristen shifted forward onto her knees, still on the bed. My bed is on risers, which makes the side of it at an almost perfect hip-height. I stood beside it as Kristen eagerly swallowed the length of me, sucking eagerly, mouth wet and wanting, making those little gulping sounds as she swallows and sucks. Her back arched high as she was on her hands and knees low, low enough to get to my cock at hip-level as I stood at the side, her knees apart, exposing her pussy to Gabrielle, who was behind her now, gripping her ass with both hands, smacking it a little, rubbing, until finally lowering her mouth down to Kristen’s pussy.

Kristen moaned. She is one of those people who is not so good at the famous 69 position, for example, because she gets too distracted by what’s happening to her pussy to concentrate on what’s in front of her mouth. I also know, however, that sometimes she doesn’t have to concentrate on her mouth—I can just slide my cock in and out and use it like another hole to fuck. And so I did. Slid it in and out, gripped the back of her head gently to use to pump my hips, and Kristen went even more limp, relaxing, her body opening.

It didn’t take long before she was shaking and crying out, muffled behind her full mouth, pressing her body back against Gabrielle and sputtering as she came. I lifted her mouth up to mine and she sat up high on her knees, kissing me.

“Get down,” I told her. She shifted, knees still shaky, off of the bed so she stood next to it with me. I kissed her again and then quickly turned her around and bent her over the side of it, pressing her back with my hand and opening up her pussy with my other hand, guiding my cock in, so wet and easy, and started fucking her.

Gabrielle was on the other side of the bed, watching. A nice show for our guest.

I started slow with a few strokes to get my cock nice and wet, then went for it, thrusting hard, not stopping, not too fast yet but hard, deeper, listening to her cry out, hands grasping for the bed, gripping the sheets and thrashing as I speed up, thicker and hard, moving the bed inches across the hardwood floor. I took a firm hold on her hips, then brought one hand around to her clit and she exploded, coming hard, squirting all over the side of the bed, down my legs, onto the floor.

Shaky, we disentangled and she climbed back up onto the bed where Gabrielle was waiting. I wiped down my legs quickly as they kissed again, curled up with each other a little.

What happened next is a little bit of a blur. Gabrielle relaxed a little, by which I mean she relaxed out of her toppy-ness and let us both touch her a little more. I kissed Gabrielle, unhooked her bra, pulled off her panties as she lay on the bed next to Kristen. She seemed a little self-conscious, but I loved the sight of the curves of her, her small round belly, her thighs, her tits, a little larger than Kristen’s but still close to the same size, both of them smaller than me but not exactly skinny. Enough flesh to grab on to, enough to grip, enough so that there is padding between us and I am not worried about being too heavy and accidentally doing some damage. I worry enough about damage as it is; I want to fuck a girl who, I can tell, can hold her own.

After I took Gabrielle’s last pieces of clothing off, she layed back on the bed next to Kristen again and they kissed, touched each other, as I worked my fingers in Gabrielle’s cunt, softly at first, just exploring, to see if she wanted to be touched, then harder and deeper as she opened up and spread her legs, breathing heavier and still kissing Kristen. She gasped a little as I worked in two fingers, then three. Kristen started writhing in response to Gabrielle: flushed, hips pushing against my hand. Kristen moaned, rubbing her thighs together and pressing closer to Gabrielle, stealing glances at me, which I took as an invitation and brought my left hand up to Kristen, too, finding her wet, happy to get touched again. Fingers in both of them, working in and out, slowly, easily, as Gabrielle gasped and they kept kissing, hands on each other everywhere, tongues in and out of each other’s mouths.

“I think I want her to fuck me,” Gabrielle finally said to Kristen.

“Oh?” Kristen asked back. “She is pretty good at that. I recommend it.”

(This is the kind of banter we’d had all night.)

“That’s how it seems!”

“You could ask for it.”

“How?”

(You guys, I’m sitting right here. Also, holy shit. )

“You could say … I want your cock. Or you could say, please fuck me. Or you could say, would you pretty please put that cock in my pussy?”

Gabrielle finally turns to me. I was barely holding myself up on my knees and have leaned back against the footboard of the bed. “Would you please … fuck me?” she asks.

I try to maintain my cool. “Uh, yes, of course.”

“Would you use a different one? That one is too … much.”

“Sure.” I was thinking I’d change cocks regardless, not so smart to share toys. I swapped out the harness and cock for a slightly smaller cock and rubber harness (easier to clean). Went over to the side of the bed Gabrielle was on and kissed her again, pulled her against me, ran my hands along her body to get used to touching her. Kristen watched. Gabrielle put one hand to my cock and looked at it, then looked up at me, and I pushed her back and pressed open her thighs, slid inside her easily.

“Go slow,” she urged. She doesn’t get penetrated too often. Usually a top, I’d found out. It makes more sense why she was seducing Kristen, then, and why I was a little confused earlier. But she was the kind of top who liked to get fucked after topping, she said. Made for the best orgasms that way.

I went slow. Gabrielle turned and embraced Kristen again, kissing more, hands on each other’s bodies, breasts, skin, as I knelt and grabbed Gabrielle’s inner thighs, pulled us together and apart as I worked inside of her. Lubed up my thumb and touched her clit.

“Fuck,” she moaned, still kissing Kristen. I guessed I had the right spot. I don’t know her body, I can’t quite tell. Soft, but a little faster, I kept going. “Fuck, fuck,” she breathed, faster, swearing, “Oh god oh god oh,” as I flicked my fingers against her clit and my hips against her, until she yelled a string of fuck fuck fuck fuck! and let go of Kristen to grip the headboard, pushing against me, harder, laughing and flushed, skin pink with a thin layer of sweat.

“I come and you just keep going,” she breathed. She didn’t seem to mind, and was not pushing me away, but rather keeping me right there, rocking against me, her hips working in rhythm with mine. I laughed, and let up.

Kristen was starry eyed, looking a little like someone had just thrown her a surprise birthday party, thrilled and thrown off. I detangled from Gabrielle and went over to the side of the bed where Kristen was and we three held each other, stroking our skin, laughing for a little while, until Gabrielle decided it was time to get going. We called a cab for her, walked her to the front door at 4am, and called it a night.

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17 Comments


  1. Lots of amazing visuals in that description! Thanks for making me want to do research even less, Sinclair…

  2. What green-eyed girl said….. And also… wow! SO HOT! :)

  3. Wow, this was nice. So many beautiful descriptions. This is the kind of fuck-story I strive to write (and live.) Thanks for sharing it.

  4. GODDAMN, sir!!! Jesus Christ that was so unbearably hot!

  5. …there are really no words…

    You realize everyone who reads this is gonna have a serious case of life-envy, yeah?

  6. so incredible. i need to stop reading at work though. too much drooling. customers stare.. :)

  7. I've been thinking about this ever since it popped up in my google reader. Incredibly, incredibly hot. I'm glad Gabrielle gave you permission to write about it.

  8. Wow. I am so envious of Gabrielle right now I could die. *swoon*

  9. I've missed your writing Sinclair, this is a fantastic return to what I love most about your blog.

  10. Woohoo good for you two! It's always good to hear that everyone had fun.

  11. superb in every way. just one small quirk that always works better for me. it's spelt 'cums'.

  12. What Ali said… sigh…

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