Austin's First Time

Austin and I have been friends forever. We talk about anything and everything. I talk to him about failed dates and he tells me about his most recent conquest. Ours is a friendship born of an awkward attempt at something deeper that just didn't work out. But even the best of friends have secrets.

He knows most of mine... including my darker side that sends me to a local kink club from time to time. But he doesn't know it all. I know he is curious... but he doesn't ask, so I don't tell. I am sure he has a few secrets of his own. But I never could have imagined what he told me after a few glasses of wine one night...

"I think I might be gay." Austin stated softly, staring into his glass of Merlot.

"What!?" I replied, more than just a little bit shocked. "Why do you think that?"

"I have been wondering what it would feel like... you know." he says slowly, still staring at the wine, unable or unwilling to look at me.

"No, no, I am pretty sure I don't know, Austin...what exactly are you talking about?"

He takes a deep breath and lets it out slowly... "I wonder what it would be like to be with a another man... to have another man's hand on my penis and playing with my ass."

"Wow... that was unexpected." I reply, trying to think of something to say that doesn't sound lame or judgmental, while refilling my suddenly empty glass.

"But I don't think you're gay."

"You don't?"

"NO!, I mean, shit... you like women right? You get turned on by women."

"Yeah, right, I do...but..."

"Well then, you aren't gay." I try to sound authoritative, "I think it makes you bi-curious."

"What do you think I should do about it?"

"Explore your feelings of course.", I state as matter of fact as possible, my mind still reeling.

"And how do I go about that?"

"Shit Austin! I don't know!" I'm going to lose it at this rate. There are a few minutes of awkward silence while I try to think of something. An idea comes to mind, but it will mean revealing a revelation of my own.

"O-Kay, tell you what... I know someone from the club... He'll be able to help."

"That kink club you go to?" Austin's eyes get big as the idea sinks in.

"Yeah... His name is Jake... he's a Dom, he's bi, and I trust him."

"How do you know him?"

Now it's my turn to be uncomfortably quiet and stare at my glass. "He tops for me at the club."

"What do you mean?"

"He's my Dom, just at the club, once in a while." God, this could go bad in so many ways.

"A Dom... as in beat me, whip me, fuck me?"

I answer with a nod, "Kind of"

"So that makes you...?"

"A submissive."

We continued the conversation until the bottle of wine was empty. It actually felt pretty good to get all that out in the open. Mark agreed to come to the club and meet Jake, after I agreed to talk with him ahead of time and explain the situation.

Two weeks later...

Austin and Jake have met and agreed to a session. I was shocked again to find out Austin wanted me there as well. I had an Oh. My. God. moment. One of my fantasies has always been to be with two bi-sexual men. The thought of two fit, gorgeous men together, touching each other, exploring each other... No way I was missing out on that shit... no fucking way.

We arrived at the club, signed the necessary paperwork, discussed the ground rules, and made sure Jake knew our safe words. Of course Jake already knows mine.

We entered the room reserved for the scene. It looks like a very nice bedroom. A king-size bed, plush comforter. Tastefully done in burgundy and cream, complete with curtains over non-existent windows. I take a seat in an overstuffed chair in the corner... content for now to be an observer.

I can tell Austin was nervous. He is pale, even trembling. Jake, in contrast, is as smooth and confident as ever. He stands before Austin and puts his hands on Austin's broad shoulders.

"We have discussed this, correct?" Jake asks. Austin nods in agreement.

"I need you to tell me out loud, not just nod."

"Yes, sorry, yes, we discussed it." Austin manages to say.

"You understand the safe word, and it's use?"

"Yes, I do."

"You have been doing as I instructed you to to help prepare for this?"

"Yes, I have." Austin says with an audible gulp, his voice becoming hoarse.

I know Jake had instructed him to use a butt plug to help him be able to accept Jake's cock, if it went that far. I wasn't sure I could stay for that if it did.

Jake tells Austin to undress, and he begins to remove his own clothes as well. The sight of these two is staggering.

They are equal in height, Austin only a little smaller in build than Jake, but just as impressive. Both tan and fit. Austin's brown hair and eyes a direct contrast to Jake's ice blue eyes and blond hair.

When they are both naked, Jake approaches Austin. He stands in front of him, no more than a foot of space between them.

Jake places a hand on Austin's broad chest, and runs it slowly down, over his taught abs and belly, stopping short of his already semi-erect cock.

He places his other hand on Austin's shoulder, and runs it down his arm... alternating with his other hand. Back and forth it went, Jake moving around Austin, caressing his body, letting him become accustomed to being touched, more than casually, but not yet intimately.

"Touch me." Jake says softly. Austin hesitates, but then raises his hands, places them on Jake's shoulders, and begins to do as Jake has been. Austin closes his eyes and takes a small step closer to Jake, and then another. Their bodies touch and Austin's eyes snap open, a gasp of breath from his lips.

Jake takes a deep breath and lets his hands roam further down Austin's body. Down to where his erection now springs proudly from his body.

Austin, like Jake, keeps his groin bare. Jake wraps a large hand around Austin's hard cock, and I hear Austin groan. "Oh my God, that feels so good."

He closes his eyes again and I can tell he is trying to get control of himself. Jake senses it as well, and just holds him, not moving. Austin tentatively takes Jake's hard shaft in his hand.

Jake whisperes something in Austin's ear, and he smiles. He visibly relaxes, and Jake starts to stroke Austin's cock. Austin is stroking Jake's, watching with rapt attention.

I realize that I have been holding my breath. I'm going to forget to breath and suffocate right here... and die happy. Is that possible? Probably not. I shake my head to clear the stupid thoughts. Lack of oxygen making me crazy. They are such a beautiful sight, it is so much better than any fantasy I have ever dreamed.

I realize something else... my panties are drenched. My pussy so swollen and hot, I am on fire. I undo the button and fly of my shorts and slide my hand inside...

Jake says something else to Austin, and turns him toward the bed. Austin bends over and places his hands on the edge of the mattress.

Jake stands beside him, and runs his hand over Austin's ass. One cheek, then the other. Over and over. When he finally puts his fingers on Austin's puckered hole Austin groans loudly.

I see him shudder at the feeling and his straining cock jerks. Jake keeps touching Austin's asshole until he relaxes once again. Then it was time to move on...

Putting lube on his fingers, Jake plays with Austin's ass again... the new sensations make him jerk away. Jake holds him firmly... speaks low... reassuring him that he will take care of him. "It's alright, relax, just feel."

As Jake teases Austin's ass he also reaches around and strokes his cock... His large, firm hand grips him tightly... familiar and foreign at the same time..."Oh God... I... too much." his face tense, flushed.

He pushes a finger past the tight ring of Austin's asshole, twisting... pumping it, in and out...whispering for Austin to relax. "It's O-kay, I've got you." Another finger. Austin is moving now, flexing his hips in time to Jake's strokes, fucking his hand.

Jake scissors his fingers in Austin's ass, increasing the pressure... massaging his prostate.. Austin moans, lost in sensation...

I am sitting in the chair in the corner, watching, playing with my dripping pussy. I know Austin is going to cum soon. It's overwhelming. I rise from the chair, no longer able to sit and observe. I remove my clothes and get on the bed and lay down, sliding under Austin so he can lick my pussy..."Oh yes, suck my clit baby."

Jake is ramming his fingers in and out of Austin's ass now, and pumping his turgid cock hard and fast. I want that cock in me, so I slide further down so he can enter me... and he does, with one hard thrust, and then stills. "God, don't move, please don't move." he whispers, his voice ragged and throaty with passion, eyes closed tight.

Jake moves off the bed and stands behind Austin... gripping his hips. I hear the sound of a condom being opened, then the click of a bottle of lube. Jake puts head of his huge cock at Austin's entrance and he pushes slowly in. Austin's hips buck, he's groaning non-stop now, God it's turning me on so much.

"Oh God...fuck...so good..FUCK!"

Jake keeps pushing in, and then backing out... in again, a little further each time... Finally, I know he's all the way in. The look on Austin's face is incredible. Lust, wonder and something I can't fathom reflected in his eyes.

"Austin" Jake says, his own voice gruff, "You set the pace, I don't want to hurt you." Austin begins to move, slowly at first, short strokes, his eyes shut tight. "God, I want this to last!" he grinds out between clenched teeth. He moves faster with longer thrusts.

I can't last... I cum hard, arching my back, my hands on Austin's shoulders , nails biting into his flesh. My pussy clenching his cock, pulsing, milking it.

Austin cums next with a roar, I feel his hot cum filling my pussy as he plunges in one last time. "Fuck, fuck FUCK!"

Jake follows with a shout of his own, filling the condom with hot cum. Wringing out his own release stroke by stroke.

Soon we are a pile of hot, jellied, sweat glistened bodies, panting for breath.

One month later...

Austin and I have made appointments with Jake a couple of more times. It's been fantastic. Austin and I have been together alone also, and it seems to be working well. Maybe the initial experience gave us a special bond. I still see Jake on my own, when the need arises. But that is a story for another time.