Your First Time Ch. 01

You arrive at the bar at 9 PM, as instructed. The joint is dismal, with only a few cars parked out front. This both relieves and disappoints you somehow.

Upon entering, you find he has already arrived, sitting in an intimate booth near the back. He spots you immediately, rising from his seat, but does not come over to greet you. You find this odd, but smile and try to ignore it. You strut over to him, flipping your hair back over your shoulders, attempting to exude as much confidence as you possibly can.

"Hel-" you begin to say, but before you can even make out half the word, he cuts you off.

"Sit." His eyes tell you not to disobey. You begin to sit across from him, your back facing the patrons seated at the bar. You knew what you were there for, but you assumed the evening would begin with at least a little awkward small talk or something. "No, no. Right here." He motions to the side he was just sitting in, and you do as you're told, timidly shuffling into the booth. He follows, careful not to brush against you as he sits.

"You look...nice," he says, almost disdainfully, as his eyes scan your ensemble.

You wish you would have worn something else, something sexier. You almost subconsciously cross your legs underneath your knee-length, loose, almost child-like skirt. "Thank you," you choke out.

"So, I'm aware that this is the first time you've ever done anything like this," he continues. You nod uneasily. "But you understand the process, I'm sure. You will do anything and everything I tell you to, no questions. No excuses." You nod again, slower this time. "You do, however, always hold the right to say no. I cannot take that away from you. Just know that if you decide to take that avenue, I will have to put an end to the evening. I'm not here for small talk."

"I understand," you say, glad to know that it's never too late to back out.

"But you know," he says, his eyes almost devilish above his glass, "from what you've said, I don't think you'll be wanting to leave." You shift uncomfortably in your seat, a mixture of excitement and fear brewing within you, trying to rack your brain for all of the bits of information you shared with this man online over the past few weeks. "So, what can I get you to drink?"

You snap out of the trance you were lodged in as his words bring you back to the present. "Um...Vodka cranberry is fine." You force an awkward smile.

"Vodka cranberry it is. But first..." he digs into his jacket pocket, resurfacing with a small plug. Your heart skips a beat when you see it. He leans in close, placing the plug in your hand and whispering, "This had better be in your ass by the time I return, and I do not want you leaving this booth. I will be watching." With that, he gets up and walks over to the bar.

You're left staring blankly after him, dumbstruck. It takes you a minute or two to realize the reality of the situation you've put yourself in. At this point, he has already reached the bar, and was chatting to another man as he awaited the bartender's attention, eyes never leaving your booth. He subtly taps his wrist, hurrying you along and snapping you out of your bewildered state.

You glance around the bar: no eyes on you. You hesitantly lower your hands under the table, pulling up your skirt. Sliding down in your seat just enough to give yourself access, you pull aside the string of your thong. Spreading your legs to provide an easier target, you take the butt plug and ease it into your hole, wincing. As you slide it in, you see his eyes locked on your body, a sneer playing on his lips. You look away.

As you drop your thong back between your ass cheeks, the pressure the plug forces on your asshole deepens just a bit. That pressure is amplified even more as you slide back up into a normal sitting position, however, and you can't help but grimace at the discomfort.

"Good girl." He has returned, drinks in hand, a proud smile across his face. You feel your cheeks warm a bit at the words of appraisal, and you look away. "No, no. I'm proud. That must not have been easy for your very first act of exhibitionism. But you must know, it only gets harder from here." The kind words make you smile, but the realization that the evening has only just begun elicits a sickening pit in the bottom of your stomach.

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Author's Note: I was quite interested in trying my hand at this type of writing. Just a short preview. Will be adding more soon.