Four Guys to Choose From

My name is Elaine, I’m thirty two years old and single. Somehow I never got into long term relationships, instead preferring to hook up with boys as and when I wanted them.

Tonight I’m visiting a group of guys. “Let’s just be clear,” I state, “only one of you gets to have sex with me tonight.” I can see in their reactions that they’re both excited at the prospect and a little confused by what the criteria of my choosing will be. I decide to offer a little leeway, “Or maybe two.”

We’re sitting on cushions on the tiny fire escape of a guy named Mark who I first solicited to get four of his friends together for tonight’s little party. He’s kindly arranged an ice bucket with beers and white wine. I decide to stick to the wine so as to play up my feminine role in tonight’s play. The guys are all in their twenties, one is named Samuel (not Sam), another is named Beaux and there’s one whose name I didn’t get — let’s call him Steve for now.

We chat amiably about the weather, how nice the fire escape is at night, each of our home towns and whether we’d go back for high school reunions or not. All the time I’m quietly assessing them, trying to figure out who I’ll take into Mark’s room and who would be left out here to listen to my moans through the window.

Samuel is the first to turn the conversation to sex, “So, Elaine — what’s the rules for who gets to sleep with you tonight?”

“I’m not sure yet,” I say, “But you get two points for being the first to ask.” I lean over and toast his beer with my wine glass. We all laugh.

In truth my plan is already clear in my head. I’m not here to have sex with the most attractive guy, nor the one I’m most interested in. I’m looking for the one who looks like he can fuck the hardest; the one who’ll make the others jealous. That’s part one of the plan.

The conversation continues at pace as the guys take turns to either tell stories (to impress me?) or to ask veiled questions to try to figure out what they need to do to be the one to stick his dick in my cunt. I tease them relentlessly, “Ooo, you’re getting me all wet!” and “Keep that up and I’ll be gagging on your cock in no time.” All the while I watch them, enjoying their reactions and their youthful bravado. I can tell that their jeans are uncomfortable, squashing their erections. But they dare not move for fear that they would reveal themselves. None of them touch me but I freely reach out and feel either their muscles or stubble.

As the evening progresses it becomes clear that Beaux will be tonight’s fuck, he’s brutish and muscular and not particularly interesting. He’ll be easy to discard once I’m done with him. But, in truth, it’s whatshisname/Steve who interests me. He’s quieter than the rest but more confident in that calm way that suggests that he’s not desperate. I like that.

And then I drain my third glass of wine and say, “Ok, I’ve made up my mind. Beaux, you’re the lucky guy. Let’s go!” There are cheers all round and Beaux is positively glowing. I get up and take him by the hand so as to make a show of dragging him through the window before turning to say, “Now the rest of you boys just be patient and wait here, ok?” The left-behind’s are quiet and I look directly at Steve, there’s not a trace of dejection in his smile.

Just before I close the door I call out to the host, “Hey Mark, there are condoms in here, right?”

“Yeah, absolutely,” he replies “In the bathroom cabinet.”

Beaux turns out alright. He gets out his cock which is already hard and I sit down on the bed and suck him off for a while. Then he pulls off my clothes and he pushes me onto the bed on my back before getting down on his knees and licking my clit. I close my eyes and stretch out like a cat to enjoy his rough tongue running up and down my labia. Then he fucks me really well, first on my back and then flipping me over onto all fours. His pelvis slams into my buttocks so that my whole body reverberates. We both make sure to moan loudly and I call out encouragement for him to “Fuck harder!” and “Just like that baby, don’t stop!” so as to be sure that the others can hear us. After I’ve come he pulls off the condom and ejaculates on my buttocks.

I collapse on the bed and, after catching my breath, turn to face him. “Thanks Beaux, that was great. Now be a darling and send Mark in here.” He grins, pulls on his pants and leaves. I can hear cheers and whistling outside as Beaux conveys the good news. And then Mark comes into the room and I wiggle my ass at him, “Your turn big boy — to say thank you for hosting us tonight.”

Mark wastes no time in getting undressed and proceeds to enter me from behind. He’s an ok fuck — not as muscular as Beaux — but I don’t come. Just as I hear his moans reaching a crescendo I quickly push him out of me, flip around and pull of the condom. “Ok now come in my mouth,” I instruct and he does.

Once we’re done I head to the bathroom adjacent to the bedroom to clean up and get dressed. Then I go back out to the fire escape where the guys are waiting. Beaux and Mark are beaming and I can clearly see that they somehow feel elevated above the others.

“Phew!” I exclaim as I straighten my hair, “Thank you guys, that was great.”

Mark and Beaux offer compliments and thank you’s.

“Now if you’ll excuse me, I have to get going.”

They all get up to walk me to the door when I stop and say, “Oh, one more thing,” I look directly at whatshisname/Steve. “Can I have your number? I’d like to invite you over to my place.”

And with that I can see that they all understand that he’s won the night and I can see that he’s going to be a fantastic lay and that he’ll make me come more than once. 
I can already smell the faintly salty scent of his skin.