It’s been a couple of weeks since you went to the Dungeon. When you get home from work, you check the Dungeon’s schedule on your computer. You don’t want to take time off, like you did the first time, and Mistress Alanis’s offer of a “lunch time special” is tempting but you don’t want to go back to the office, smelling of sex or walking funny. You would rather be able to go straight home. That limits your options, if you want to stay with Mistress Alanis. There are other Mistresses and Masters who have that afternoon time spot open, but you don’t want to try someone else, not just yet. She seemed to understand what you were looking for.
Checking the schedule, you see that on Thursday this week, she has an hour open in her schedule in the afternoon. You take a moment and think about when you leave the office, travel time, possible traffic delays, and leave enough time to play. You click on the box and just reserve the bottom half of the hour. In the notes area, you type “I want to explore receiving anal, like we discussed. Some paddling, and use of a gag if you think it works for the “sex toy prisoner” fantasy. I will remember to wear old clothing for you to cut off. See you Thursday Afternoon.” You send it and your payment for the session in advance. That night you masturbate, imagining being tied up, your butt spanked, and a lubed finger working in and out of your helpless ass.
Thursday morning, after you dress for work, you pack a gym bag. In it you put a pair of old sweat pants, a stained t-shirt, a pair of drawers with holes in them, and a towel. If anyone asks, you can tell them that you are going to the gym and this is your workout bag.
As you get to the last half hour of the work day, you log off and tell your boss that you need to go and change for the gym. He looks up from his monitor, “Going to the gym? Good to hear. Workouts are good for your physical and mental health. If you need a workout buddy, tell me. My wife keeps asking me to start working out.”
A worried feeling comes over you for a moment. “A workout buddy? Ummm. I don’t know. I have a personal trainer I just started using.”
“Ok. Good for you. If your trainer has an opening for more clients tell me. What’s his name?”
“Her name is Alanis.” You say confidently.
“Oh, a female trainer. My wife wouldn’t agree to that.” He pauses for a moment “Is she good looking?”
You smile broadly “She is the kind of woman that men spend money to get extra time from her.” Then you wink and make an hourglass motion with your hands, like you have seen guys do in old movies.
Your boss lets out a slow whistle and shakes his head. “Nope. I’d rather be fat and married than have my wife leave me for that. Go enjoy your workout. Remember that the company health plan authorizes discounts on gym memberships. Ask your trainer if she takes our health insurance.”
You nod as you smile and leave his doorway. You chuckle to yourself as you head for the Men’s room to change. “I doubt Mistress Alanis would give me a discount because of our insurance plan. Worse, how would I tell the insurance company that I require weekly sessions with a professional Dominatrix for my mental and physical health?” You think to yourself as you undress, roll up your work clothes, and pull on your “workout” clothes. Checking your watch, you see you have about an hour to get over there.
Pulling into the parking lot, you check your watch again, you have plenty of time to enter. So, you grab your gym bag and walk up. The heavy wooden door still looks so imposing and dark as you approach. The dark weathered stone and the oak door with black iron hardware looks so scary, that even though you know what’s behind it, you feel a tingle of fear, which heightens your feeling of arousal too.
Stepping inside, the office decor, still strikes you as odd, but not unpleasant. The receptionist greets you, as she motions for you to sit on one of the chair lining the wall. “Sir, you are a bit early, so please wait. But before you sit down, may I please inspect your bag? It is just for the safety of the staff.”
You nod and step up to the desk, open the gym bag, and let her look inside. She asks you to unroll your clothing to ensure that there is nothing dangerous hidden. You do as she asks and joke “Wouldn’t a metal detector or x-ray machine be easier?”
She frowns, “Sir, how would that look if I had more security here than an airport?”
You think about it as you re-roll your clothing and put it back in the bag. “I understand. What should I do next time?” you ask, genuinely curious.
“Sir, many of our clients who choose to bring items into the rooms, use a bag that is clear and see-through. If you ask your Mistress, she might be able to suggest something, unless you wish to rent one of our storage lockers?”
“Storage lockers? Like at a gym?” You ask.
She nods and points to an unmarked door off to the right. “We offer rental lockers for our regular clients.”
You nod and sit down in one of the chairs along the wall. “That makes sense. Some people might have items that they don’t want to carry back and forth, or have in a see-through bag.”
“Yes, sir. Oh. There is a note on your account. Your Mistress, wants to verify that you came ready and don’t need prep time prior to your session.” She says pointing to her screen.
You tap your gym bag, “I’m ready. That’s why I have clothes to change into afterwards.”
She returns back to her screen. “Very good Sir. Please wait, and when it is your time, her assistant will come for you.”
You pull out your cell phone and play a game to help pass the time. You just now realized how this reception area reminds you of the waiting room of a doctor’s or dentist’s office. Including that faint smell of disinfectant and the hum of the air conditioner.
You completed a couple more levels on your flower-matching game when you feel a hand on your shoulder. You look up and see the man in the gimp outfit from last time. Silently he nods and motions for you to follow him. Grabbing your bag, you turn off your phone and follow. You go down the same hall as last time, but stop at a different door. He holds it open and motions for you to enter. This room is similar to the other one, in that you see the candles, iron sconces, and chains attached to the wall. In the center of the room is a massage table with padded cuffs at the corners and extended bars on two of the corners. You aren’t sure what they are for, but you don’t want to ask any questions. The Gimp motions for you to set your bag by the sink area and then lie face up on the table.
He secures your wrists and ankles, then puts a ball gag in your mouth. The whole time never saying a word. You feel the strength in his hands as he secures you, and are aroused as he makes you helpless. Then he leaves silently. This time you aren’t blindfolded so you look around.
The shadows caused by the candles, move against the walls. You realize just how dark it is and how deep the shadows really are. They could hide anything or anyone. You notice a couple of small tables with some items on them but you aren’t sure what they are because they are in the shadows.
The door opens and you hear the click of high heels on the stone floor. “So we have captured you again. Or maybe you want to be my prisoner…..used as my personal sex toy?”
She is wearing tall, black stiletto boots that go up to her thighs, along with black PVC corset and very short PVC skirt. She has a paddle in her hand and smacks her palm with it. As she stands there, silhouetted by the candle light, she is everything you have dreamed of. You feel your erection grow in your sweatpants.
She sets down the paddle and picks up a pair of scissors from a table. The silver glints and reflects the candlelight as she opens and closes them. Snip-Snip.
She gets really close to you, and slowly caresses your cheek with the blade of the closed scissors. “You have on entirely too much clothing. My toys should be naked and ready for me to use.” She says in a sultry tone.
You feel her pull the neck of your t-shirt away from your body as she opens the scissors and cuts right down the center of your shirt in a single motion. She places her hand on your chest. “Mmmmm Look at those nipples of yours. So hard. So excited. Maybe I should suck on them before I move down?”
You try to say something but the gag prevents you from making any other noises aside from grunts. She slowly licks around your left nipple and then you feel her suck it firmly. You’ve never had a woman do that to you before. It feels so different and exciting.
“I’ll save the other one for later.” She says as she picks the shears up again. Moving down to your sweatpants, she grabs the waist band and then cuts all the way down to your left ankle.
“Awww, you have on underwear. And look at that tent.” She says in a playful tone. She steps away and puts on a pair of surgical gloves. She returns with a bottle of lube. Pulling your cock through the fly, she drips lube on it and strokes it up and down. “Look how nice and hard you are. A perfect toy for me to use.” She strokes you slowly at first and then does a twisting-grip motion around the tip. You grunt in pleasure.
“This looks so tasty. But I think I want to see your ass first.” She says. She unclips the chains at your ankles and connects then to the upright bars at the corners, raising your legs up and forcing your ass to the edge of the table.
You feel the scissors slowly cut your underwear along the crack of your ass, leaving you open and exposed. “Mmmmm that is a sexy ass. Do you know what I do to sexy asses, Prisoner?”
You try to say “No Mistress, what?” but you make a muffled grunt.
You feel cold lube drip down the crack of your ass, and then a gloved hand rubbing it all around. “I need to check to make sure you aren’t hiding anything. An asshole is very pliant and stretchable. A prisoner could hide all sorts of things there.”
You feel the tip of her finger rub around your crinkled ring, and then open it. She slowly works it back and forth, going a little deeper each time. “Mmmmmm your asshole is so tight.”
As she goes deeper, your cock feels so hard against your bare stomach. “My-my, look how excited you are. I wonder what happens if I stroke you with one hand and finger you with the other?”
You feel a gloved grip your shaft as the finger of her other hand thrusts in and out of your lubed ass. She goes slowly, letting you feel texture of her gloved finger as it works your ass. Her other hand moves up and down your slick shaft in tempo.
This feels so good. You pull against the restraints so you can help, but the cuffs hold you firmly. “You are enjoying this, aren’t you. Should I just stroke my captive toy until you cum, or should I pleasure myself first?”
You try to say “Whatever you want, Mistress” but you just grunt and drool down your chin.
She has her finger all the way in your ass and starts to finger-fuck you faster. She keeps the same tempo stroking your hard cock.
“You are so slick, now. You won’t last long.” You hear her say in a seductive tone. You close your eyes and wish any of your previous girlfriends would have been this adventurous with you. Their faces flash before you, Heather, Traci, Jacki, and Jennifer, all of which thought that anal play was “dirty” or “gay”. You try to close your mouth around the ball gag, as you feel pleasure move though you, and you shoot cum on your stomach and chest.
She withdraws her finger and releases your shaft as cum continues to spurt and drip from the tip on to you. You hear her pull off the gloves and throw them away. She walks up to your head and removes the gag. “Mmmmm My little prisoner. You really enjoyed that.”
You stretch your mouth for a moment, as you realize how tight the muscles in your jaw got from you biting on the gag. “Yes, Mistress. That was amazing. Do you need me to lick your pussy, or do you want to ride me?” You ask.
She raises her skirt and shows you that she isn’t wearing panties. “That sounds so tempting but, we are out of time.”
She wipes her finger along her damp pussy lips and then rubs her wet finger along your lips. “Here is a taste of what you missed this time. Next time book the full hour.” She says with a wink.
You lick your lips and taste a hint of her flavor, reminding you of last time. “I will Mistress.”
She uncuffs you and then heads to the sink to wash up. You pull off the remnants of your clothes and walk over to your gym bag.
As she dries her hands, she says. “If you really want to get into anal play, do a little research and prep. Professionals modify their diets, take enemas prior to getting on camera, and make sure that they are clean inside. I know this was your first time, and I was gloved. But you might want to more thoroughly clean your ass if you want more than just a gloved finger in there.”
As you wipe the lube off your ass with your towel, you see a streak on it. “Oh. I’m sorry Mistress. I didn’t know. I’ll do better next time.”
She walks closer to you and kisses your cheek. “I know you will my little prisoner. Remember to be nice and clean and to schedule enough time for everything you want.” She pulls a thick cotton robe off the hanger on the wall and wraps it around her, hiding the sexy PVC outfit.
“I am learning so much from you. Thank you.” You say as you pull on your work clothes.
She smiles “It’s what you pay me for. See you next time.” And then she walks out of the room leaving the door open.
As you pull on your shoes, you think “Yes, I will see you next time.”
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