Adventurous Me (7 page)

“Hey, can I ask you something?”

“Sure, baby.”

“Do you think I’m boring?”

Dave lets loose a belly laugh. “Honey, you’re a lot of things, but boring isn’t one of them. Tomorrow night, I fuck your ass. And I guarantee the last thing I’ll think is that you’re boring!”

He’s going to fuck my ass. I’m scared to death. And very, very excited.

I get a big surprise the next night when I get there. Big surprise. Really huge. Something I never could’ve expected.

“I’ve got a little emergency. I’ve got to go pick up my daughter and take her to the hospital. Her husband was hurt in an accident about fifteen minutes ago,” Dave tells me absent-mindedly, and he’s scurrying around the private room where we meet. “So I asked someone else to work with you tonight. I hope you don’t mind, sweetie.”

I shake my head. “If you trust him enough to ask, then I trust your judgment enough to trust him.”

He nods. “This guy is the most trustworthy person I’ve ever met. I’d trust him with my life – and yours. He’ll be here in about ten minutes, and he knows he’s supposed to work with you. Just go on out to the bar and he’ll come and get you.”

“Who is . . .” Before I can ask, he’s out the door.

I straggle back out to the bar and ask for a cosmo. I’m sitting there, listening to the music, inspecting my nails, when I hear someone say, “Trish? Aren’t you Trish?”

I turn and I can’t believe my eyes.

It’s Clint.

All I can manage to stammer is, “Uh, yeah, Trish, um, yeah. Uh . . .”

He sticks out his hand for me to shake. “I’m Clint. Dave asked me to work with you tonight.”

“Um, sure.” My face is reddening. As I shake his hand, I can feel my cheeks burning. And I must look like a complete imbecile.

“So if you want to finish your drink in the private room, we can get started.” I’m more than a little off kilter. He’s being very professional about the whole thing, not rude, just not very warm.

“Look, Clint, if you’re not comfortable with this, I can . . .” I can’t read the expression on his face so I add, “If you don’t want to . . .”

He shakes his head and shrugs. “Why wouldn’t I?”
Good question,
I want to say.
Why do I get the feeling that I’m getting the same look from you that you’d give a firing squad?

“Okay, so here we go, I guess.” I pick up my glass and start down the hallway. I can feel Clint right behind me. Steffen or Dave would’ve had my elbow, but he hasn’t made an effort to touch me in any way except to shake my hand.

Once we’re in the room, he sits down in a chair and I sit on the edge of the bed. “If I understood Dave correctly, your training tonight was supposed to be anal sex.”

“That’s what he said.” There’s not a sound in the room. I wait.

“Right then. So any questions before we start?” His gaze is steady. It’s like he’s looking right through me. I’m not sure he even realizes I’m in the room.

“Yeah. Is this going to hurt?” It’s the question that’s been burning in my mind.

“Your first time?”

“Yes.”

“Then yes, it will. But it’s my job to make it bearable and even pleasurable if I can, and to help you know that it will get better if you do it more often.” Still no emotion. What is it with this guy?

“So what do I need to do?” It’s almost like I’m in a doctor’s office, just kind of clinical and cold.

There’s something, a shadow of some kind, that passes over his face. “From this point on, that’s sir.”

“So what do I need to do, Sir?”

“I would appreciate it if you were not so bratty. I won’t tolerate that.”

That hurts my feelings just a little. “I’m sorry if you thought that’s what I was doing, Sir. I wasn’t. I was just practicing. I just want to please you, Sir.”

He sits there like he’s trying to decide if he should stay or run away as fast as he can. Finally, he says, “Remove all of your clothing, sub. Fold it neatly and present yourself to me.” I do as I’m told. I really do want to please him. There’s something completely unsettling about him, and it’s really screwing with my head. I wish I could put a finger on it, but I can’t.

When I’m undressed, I present myself to him just as Steffen taught me that first night, and I wait for him to tell me if I’ve done well, but he doesn’t say anything. Then he starts in.

“Anal sex is usually uncomfortable for the bottom at least the first dozen times it’s performed. It’s important that plenty of lubricant is used, and that the top takes the time to properly prepare the bottom.” Originally, I thought he meant “bottom” kind of like “butt,” but that must be what I am – a bottom. He’s a top. So I understand that. And I feel pretty smart about that, so much so that I must’ve been smiling to myself, because he stops and says, “What’s so funny, sub?”

I put on my best serious expression. “Nothing, Sir. It’s just that I understood something you said without asking what it meant, and I was pleased that I did.” By the time I finish, I know that what I’m saying doesn’t make any sense.

He doesn’t seem to care. “Good. Whatever. So it’s the top’s responsibility to properly prepare you. If ever you’re with a top or Dom and you don’t think you’ve been properly prepared, safeword and explain. Otherwise, you could be injured to the point that you’d have to have medical treatment, and no one wants that.”

“Good heavens, Sir, no. I certainly wouldn’t want that.” He makes a “harrumphing” sound until I shudder, and he must realize that I’m sincere.

“No. No one does. If a Dom doesn’t properly prepare you, he probably
thinks
he has. Let him know if that’s not the case. Now, there are two rings of muscles in the anus, one at the opening . . .” At this point, he goes into a five-minute anatomy litany. I’m not complaining; I learn a lot about the anus during this one. But I’m surprised at how thorough he is. He really is training me, not just doing it to me and hoping that I get it. I’m impressed. When he finishes, I decide a compliment is in order.

“Thank you, Sir. I enjoyed that detailed anatomy lesson.”

His face is passive, but he growls, “Impertinence is not appreciated, sub.”

I blanch. “I’m sorry, Sir. Please, I’m not being impertinent. I just wanted you to know that I feel much better, much more confident of my safety, because you’re so knowledgeable. That’s all, Sir. I’m sorry if I came off otherwise, Sir, really. That wasn’t my intent.” For some reason, I feel tears start to prick my eyes.

For the first time since we came into this room, he reaches over and places his hand on my head. “My only desire is for you to feel safe and satisfied, sub. I’m sorry if I misjudged your comments. Thank you for your confidence in me. I promise I won’t let you down.” I take a deep breath.
This is going to be okay,
I tell myself.

“Get up on the bed. On your knees, elbows on the mattress. Quickly.” I jump up and run to the bed. I try to assume the position, but it’s awkward for me. It was easier on the horse that night, but here, the mattress is too soft. Master Clint sees me struggling.

“Sub, hey, it’s okay. It’s my job to see that everything is as it should be. I can handle your position. Don’t worry about it.” I hear a snapping sound. “This is lube. It will be cold and it will be messy.” It drips down my crack and I’m sure it’s falling on the mattress. Plus it’s so cold that I shiver a little. I guess my ass wiggles when I do. There’s a loud “smack” as his hand comes down on my ass cheek, and I squeal.

“Be still; don’t move.” I feel a sensation around my tight little hole. His finger? I’m not sure. Then I feel something move into it slowly. It’s not very large, so now I’m sure it’s his finger. He pumps it in and out a couple of times. Then there’s a stretching when he presses what I imagine must be two fingers in there, and I groan.

“Okay? Good to go?” he asks.

I take a deep breath. “Yes, Sir.”

“Good.” I hear a tearing sound and start to ask, but I realize it’s probably a condom wrapper. “Understand that tonight is not about you being satisfied, and it’s unlikely that you’d have a climax from first-time anal sex anyway. This is a learning experience. But I will not let you leave here wanting. You will have an orgasm and some kind of satisfaction.”

“Yes, Sir.”

I feel him climb up onto the bed behind me, and then he grasps my hips with his hands. “I’m going to take it very slow to begin with, but before we’re finished, I expect to be fucking into your ass vigorously. It will hurt. I will, however, try to keep it from being excruciating.” I feel something against my rosette. “Your safeword?”

“Um, what should it be?” I have no idea what to tell him.

“Most subs use the traffic light approach, red for stop, yellow for slow down and discuss, green for go. Will that work for you?” he asks.

“Sure, Sir. That’s easy enough to remember.” I’m kind of excited now. I’m about to have an adventure.

That excitement fades pretty quickly. “Oh my god,” I whisper as the head of his cock pushes into me. It hurts like a motherfucker. I don’t know what to do to make it better.

There’s a resounding “crack” as his hand slaps my ass again – hard. He presses in a little, then slaps my ass once more. “Concentrate on the feel of the point of impact of my hand on your skin and try to open up for me. Push from inside. Now take a deep breath. Let it out as I move in, then take in another as I move out. Ready?”

I figure out what he means and in just a few seconds, I feel another burn as the interior ring of muscles is pushed against. When he makes it through that, I cry out. I knew it would hurt, but I didn’t know it would hurt this much. “Doing okay?” he asks.

“Yes, Sir,” I manage to pant out.

“Color?” he asks. I don’t know what he means. “Sub! Your color?”

Oh – the safeword thing. “Um, uh, greenish yellow?”

“Good. I’m about halfway in. Try to relax. I know it’s hard, but try.”
Yeah, it’s hard – you’re shoving your cock up my ass. That’s hard to relax into.
He presses harder and the burn from my anus is growing wilder. Just when I think I can’t take any more, he says, “Very good, sub. I’m all the way in.”

I’d like to say there was this enormous feeling of accomplishment, but all I could feel was some measure of relief. I feel him draw out, backing his pelvis away until just the head of his dick is inside me, and then I hear the flip cap on the lube bottle again. “I’m putting more lube on my cock. That will help,” he tells me.

When I hear the cap snap again, I know to get ready. Then he says, “Here we go, little one.”

He presses straight into me, not a fast, vigorous stroke, but a purposeful, deliberate one. I fight the urge to scream, but before I can settle into it, he pulls back out and shoves back in again. Now I really am burning, but I want to do this, I really want to. Something about him makes me want to please him.

Then he starts a steady rhythm. It isn’t fast, but it isn’t slow. It’s just steady, boring almost all the way into me and then stroking back out before burying his cock in me again. He’s been fucking me like this for about three minutes when he says, “Okay, here we go.” I shudder and brace myself.

The motion he sets up is almost perpetual. He’s moving in and out of me just like anyone would, and three minutes in I realize it doesn’t hurt that much anymore. At the seven minute mark, I realize I’m actually kind of enjoying it.

“Sub, your color!” he snaps, and I can tell he’s trying to hold back his climax.

“Green, Sir!” I’m almost joyous. I’m getting my ass fucked, and I really kind of like it. Well, more than I thought I would.

And that’s when I hear it for the first time: He groans. That sound, the sound of him enjoying my body and getting off in me, sets my entire being on fire, and I feel my skin heat up. I want it, need it, have to have it. He picks up the pace of his pounding into me and I brace myself and take it. His thrusting becomes more frantic, and then suddenly, he stiffens and grips my hips so hard that I’m sure I’ll have finger marks. Burying his cock in me as far as he can, he grinds into my ass to relieve the last of his need, and I moan out.

He collects himself somewhat, still buried in my ass. “Sub, your color?”

“Green, Sir. Very, very green.” I try not to grin.

“Good.” I can’t see his face, but he actually sounds pleased. As he pulls out of me he says, “Drop your ass and go into a presentation pose, but keep your torso down.” I try to do what he’s asking of me and I hear him snap off his condom. Once I’m down like I think he means, he says, “Now, spread your knees apart so your pussy is open.” Now I’m face down, resting on my haunches with my knees apart. I feel his hand move between my thighs from behind and then his finger is stroking my clit.

I have trouble sitting still. My hips want to grind, but the way I’m sitting keeps them from being able to move. To insure that, his hand is on my ass, pressing down hard to keep it from coming up at all, and I concentrate on his touch and the heat from his skin on mine. He speeds up his motions and I feel it, the building and gnawing sensation, and then I’m coming, my pussy throbbing and clit pulsing, and I’m trying hard to keep from asking him to stop. And all of a sudden, he does.

His hand strokes down my spine like a breath, and I sigh. “Feel okay?” he asks, his voice quiet.