I had been a big fan of bondage for many years, browsing plenty of sites for videos and pictures. I had also begun reading through the sites of more well-known pro-dommes, getting excited by all the services they had on offer. I had never gotten up the courage to actually look into contacting one of them for a session, mostly because all of the ones that I was familiar with lived in different cities or countries.

One night though I decided to search for one in my area and I was surprised to actually come across several active sites. I looked through all of them and settled on contacting one of them, just to test the waters. Mistress Caitlin was older than me, in her late thirties or early forties, but cut a beautiful figure in fetish apparel. Particularly since she was quite a bit taller than me, judging by her pictures.

I sent her an email asking about possibly booking a session with her, explaining that I had virtually no real experience with the scene. Her response was quick to arrive in my inbox; she wrote that she particularly enjoyed introducing newbies to the pleasures of bondage and that I shouldn’t be nervous about asking for what I wanted to happen. We exchanged a few more emails, nailing down a day and time for me to meet her at her dungeon and then all that was left was to wait for the day.

On the appointed day I arrived at the address she had given me. It was a high rise apartment building that I had to get buzzed into. I dialed the number she had given me via email and got to hear her voice for the first time,

“Yes?”

My voice caught as I responded, “Good…good afternoon Mistress. It’s—”

“That’s all right. Room 1012.” The door buzzed open.

I was still shaking a bit with excitement as I got onto the elevator, and the doors closed. My thoughts danced and spun with half formed fantasies of my coming session with a real dominatrix.

I stepped into the hallway and as I spotted the room number that she had given me I felt fresh tremors sneak their way down my spine. Without delay I came up to the door and knocked. The seconds I spent after that seemed like the longest in my life, as though at any moment someone might see me and know precisely what I was there to do or have done to me.

The door opened partially and her face appeared around it. She smiled at me in greeting and gestured for me to come inside, swinging the door wide as she did so. She was dressed in knee high leather boots with a short leather skirt and black leather corset completing the quintessential dominatrix look. As I entered I fumbled for my wallet, with the tribute enclosed, but she spoke first, interrupting my efforts,

“Before we get to that I want you to kiss my boots in welcome. That is how a slave greets his mistress.” The words were kindly spoken, but it was definitely an order.

I dropped to my knees in front of her, breathing a little quicker, and planted two quick kisses on the toe of her boots.

“Good boy. Now you can go into the other room and take off your clothes. Make sure they are folded neatly.” With that she turned and walked further back into the apartment.

I removed my shoes and walked down the short hall which ended with a small alcove living room space on my right, a large curtained off space directly in front of me into which Mistress Caitlin had walked, and a longer hallway on my left with three doors leading off from it. Without wasting any time I begin striping out of my clothes, slowing down a bit once I reached my underwear as this seemed to me to be the point of no return. I could see the silhouette of the dominatrix through the curtain though, standing still and waiting, so I quickly shucked them off and then walked tentatively over to the opening in the curtain.

The room beyond was her dungeon and what a dungeon it was. All manner of bondage gear and equipment was racked along the walls or set up in tandem with furniture. The entire far wall was taken up by floor to ceiling windows, giving me a pretty amazing view. But the real centre of my attention was swiftly reasserted as my eyes found their way to Mistress Caitlin once again. She was standing in front of the opening with a small smile on her face,

“Kneel down for me.”

My knees seemed to buckle of their own accord, and I sank down to them in front of her. She brought out a black leather collar from behind her back and held it in front of my face.

“This will be your slave collar for the duration of your session with me. When you wear your collar you belong to me. You are my slave to do with as I please. Do you understand?”

“Yes…Mistress,” I said in a low voice

She moved forward and slowly buckled the collar around my neck. The feel of the leather gave me goosebumps. I heard a small click from behind and she brought a key around to hold in front of my face. She had locked the collar on! This was really happening!

The clink of chain refocussed my attention on the leash that she hooked onto the front of my collar. Then, tugging at the leash to make me follow she led me over to where a chair and small table were set up near the window. She sat down on the chair and motioned for me to kneel up in front of her. A pair of leather cuffs were selected from among the implements laid out on the table, and she quickly buckled one around each of my wrists, locking the cuffs with additional padlocks.

Next she picked up an intimidating leather bondage hood from the table, “All of my slaves wear hoods in my dungeon. I realize you may be a little worried, but trust me. This will certainly enhance your experience.”

Without waiting for any response she lowered it over my head and began tightening it down. The laces in the back were cinched in and drawn tight, molding the hood to my head. There was a small opening for my eyes and mouth and two small holes for my nose. With the hood tight over my head she ran her hands all over it, smoothing any creases and calming the little bit of anxiety I had begun to feel.

“Time for you to worship my boots slave. But before we get to that, I want to make sure you aren’t going to cum everywhere from the excitement of being at a real Mistress’ feet.”

Saying this she produced a chastity device and coaxed it onto my cock and balls, locking it in place with yet another little padlock and key. Once that was done she pointed me down to begin licking and kissing her boots. I was in heaven. Finally I was getting to experience what I had been watching in all those online videos!

The whole time I was worshipping her boots she kept up a steady stream of direction and encouragement. I could already feel the chastity cage getting tighter and tighter as I responded to the situation. Whenever I spent too long on one portion of her boots I would feel an insistent tug on my leash, directing me to a new spot.

“Well, let’s see how you did slave,” She pulled me back from her boots to examine them, “Hmm. You know, for a first time submissive you are quite good at boot worship. Maybe I’ll keep you around to clean my boots for me huh? Would you like that slave?”

“I…I don’t know Mistress,” I stammered. Was this the role playing that she had talked about on her site? I hadn’t asked for any, but maybe it just became part of sessions?

“It doesn’t matter. I don’t expect a slave like you to make decisions.” She stood up and dragged me by the leash over to the bondage bench that was positioned next to the table and chair. She pulled me up into it, securing my wrists and ankles to the tie down points and leaving lying bent across it with my legs up off the ground secured tot eh sides of the bench.

She went off out of my line of sight for a few minutes. When she returned I gasped. She wore a strapon harness with a medium sized dildo attached to it, “Time for you to worship something else slut.”

Saying this she grabbed the back of my hooded head and pressed my mouth down on the strapon. I choked on it for a few moments but she began to slowly fuck my mouth with it, giving me time to get used to this foreign intruder. I began to moan as I sucked, egged on by her comments, calling me her dirty slut, and how well I was taking her dick for being such a newbie. “Maybe you’ve sucked strapons before huh? I wouldn’t be surprised you little slut.”

This went on for a while, just her continuously fucking my mouth. Finally she withdrew it but my mouth was no sooner free from the strapon then she was pushing a ball gag into it.

“MMMMMPPPH!”

“Slaves aren’t allowed to speak,” Mistress Caitlin said, still with that kind but commanding tone, “Until I can trust that you understand that, you will remain gagged unless your mouth is otherwise occupied.”

I continued to make little complaining noises through my gag, so she reached across and delivered three firm spanks across my ass, “Slaves don’t complain either.”

I stopped my whining through the gag. She patted my head like an owner congratulating a puppy on obeying and then strapped a leather blindfold onto the hood I wore, plunging me into darkness.

She walked around behind me and I suddenly felt the cold sensation of lube being spread around my ass.

“Mmmph?!”

“I’ve taken one of your holes slave. It’s only right that as your new Mistress I be given first go at all of them. Now just relax, it will go much easier for you if you just let it happen.”

I was freaking out a bit now, and began struggling against the restraints. To calm me down she grabbed a vibrator and held it against both my butt and chastity device. While she did that she began to run her hands around my asshole, occasionally gently popping a finger in. This carried on for a few minutes, and the gentleness of it calmed me down from my freakout. Maybe she had just been doing some more role playing with the whole ass fucking thing. I certainly hadn’t asked for that!

Any further thoughts along that line were swiftly disabused as she withdrew her finger and slowly began pushing the head of the strapon into my ass. I moaned and squirmed around as she pushed it in gently but firmly, inch by inch. Finally she was all the way inside me, her hips resting on my asscheeks.

“There we are slave. Your first strapon fucking. Just enjoy that feeling for a bit. Nice and full back there aren’t you?”

It was certainly a new experience for me and I was caught between warring feelings of pleasure and humiliation. I hadn’t wanted anything like this at all when I came to Mistress Caitlin, but with the ball gag and hood and blindfold, there was no way for me to do anything about it.

Then she began to move. Slowly thrusting in and out, in and out. My moans were louder now, verging on yelling as she drove the strapon into my ass. Her hands held my hips tightly, a stream of “oh yeahs” and “That’s it slut” emerging steadily from her mouth. To further add to my humiliation I could feel my cock straining hard against the chastity cage, but whether from the vibrator or strapon I couldn’t tell.

It seemed like it would go on forever, but at last her rhythm slowed and she came to a stop, still buried up to her hips in my rear. There was a series of unstrapping sounds and she stepped away from me, leaving the dildo firmly embedded in my ass.

“Just taking a bit of a break slave. I’m sure you’ll be a good little slut and hold my spot for me.” She gave my filled ass a pat and then walked off elsewhere, leaving me to stew in my humiliated state.

I was torn between being scared at the unexpected turn my supposed intro session had taken, but also incredibly turned on at the way in which she was effortlessly dominating me. Through her restraints, and hood, and gag, not to mention the leather slave collar, she had rendered me an anonymous submissive boy. Nothing more than that to anyone who happened to see the two of us in our role. That more than anything else was what fuelled my desire to continue, the fact that she was in total control. I didn’t have to ask about what I wanted, she was going to give me a BDSM session.

My thoughts down this road were interrupted as I heard the approaching boot steps of my mistress. I felt hands begin caressing my bound form, lingering over my ass and chastity caged genitals, and then making their way up to my head and neck.

“How are you enjoying your session so far slave?” She asked the question while pressing my hooded head into her crotch, “Are you happy that you are my slave?”

I mmph’d and tried to nod my head, drawing a chuckle from her. She patted my head again,

“Good. Although that doesn’t mean we are anywhere near done.”

She returned to her position behind me and eased the dildo out of my ass. I gasped as my ass suddenly felt so very empty, but then I bit down on the ball gag as she pushed a butt plug into my ass, seating it in place.

“There we are slave. That will remind you that I own your ass. Now let’s have some more fun with you hmm?”

She freed me from the bondage horse, making sure to quickly attach chains to my ankle and wrist cuffs. There was never a moment that I was not bound, although in the total darkness of the bondage hood with the ball gag on there was little I could have done. She re attached the leash to my collar and began leading me around, encouraging me to keep up on all fours. The sensation of the butt plug seated deeply in my ass made for a completely new experience while I was following her around, and it served to keep my cock straining against the cage she had placed it in. After a few circuits of the room she stopped me and I sensed that she had sat down again as I felt a boot slowly move across my chest.

“Well slave, I think I’d like some more of that wonderful boot worship you gave me earlier.” She leaned forward and unbuckled the ball gag, letting it hang around my neck as a potent reminder of how easy it would be to lose my mouth to her again. I immediately leaned forward and found her boots with my face, and began worshipping them in much the same way as before. She purred in satisfaction, making all manner of little encouraging or happy noises at my efforts. At some point She must have flipped a switch or pressed a button as the butt plug in my ass began to pulse and vibrate, drawing moans of pleasure from me in spite of myself.

“There now, my little slut likes it when his ass is owned doesn’t he?”

“Yes Mistress,” I mumbled from around her boots.

“Good boy.”

This went on in the same pattern as before. I worshipped her boots for a long time until she stopped me, inspected them, and complimented me again on my good work. Then the ball gag was reapplied tightly and I was brought back over to the bondage horse where I was tied down and then strap-on fucked again by Mistress Caitlin. I was lost now in this bondage world, no idea what to think save to go along with this incredible woman who was completely in charge of my body now. This strap-on session went on for longer than last time but finally came to an end with her removing her dildo and inserting the butt plug again. She left me there for quite a while, though I could hear her in the background moving around and getting things prepared.

“I’d like to try something with you now slave. A new restraint I think you’ll really enjoy.” Saying this she untied me from the bondage horse and unlocked all of my wrist restraints and chains. I rubbed my wrists a bit but otherwise crouched on the ground awkwardly, not sure what to do. This was solved as she firmly pressed me to kneel upright to face away from her. A procession of leather rustling and metallic clinks sounded from behind me, and then I felt both of my arms being engulfed by leather. She pulled the device up my arms and began to tighten it, bringing my arms close together. I realized at that point that this was an armbinder!

“Yes my little slave,” Mistress Caitlin responded to my surprised grunts, “An armbinder of your very own. I want to see how flexible you can be for me. And how long you can stand being in tight leather bondage for your Mistress. You do want to please me don’t you?

I mmph’d in response, I definitely wanted to please this lady. The armbinder was tightened up further, and drew my hands strictly behind my back. Now I really felt like a leather slave, completely at her mercy.

She picked up the leash and tugged me down the longer hallway that I had first seen upon entering the apartment. We entered the first room on the right, her insistent tugs positioning me along the wall before getting me to kneel down once again. My gag was unbuckled once again and I stretched my jaw in relief before the tug of the leash brought me forward, bending over at the waist. Suddenly I tasted rubber, and I realized she had a strap on in place again. I opened my mouth and began to suck, her hand on the back of my head making sure I kept up a steady rhythm up and down.

“That’s a good little slut. You like sucking my cock don’t you? And worshipping my boots for me and making them nice and clean.” I grunted as best I could with her rubber dildo bobbing in and out of my mouth. “Of course you do. Mmmmm. Yes, I definitely think I need to hang onto you slave. You are just too good to pass up.”

I moaned at the words, turned on by what I assumed was roleplay. She laughed, “I thought the idea would turn you on. You’ll be my little leather bondage slave, worshipping my boots and taking my cock. I’ll keep you tied up and hooded, with your cock in chastity except when I decide to let you have release. We’ll spend our days here in the dungeon and maybe our nights out on the town with some of my friends. How does that sound slave?”

I moaned louder and kept sucking her strap on. She laughed again and continued to talk of all the things she would have me do were she to keep me as a slave. I felt like I could just explode all over, were it not for the tight chastity cage around my cock and balls. She flipped my blindfold off and told me that since I was such a slut I should enjoy the sight of sucking cock.

She pushed me back from the strap on after a few more minutes, and I took my first breath free of rubber in quite some time. She stood up and busied herself about the room, removing the strap on harness and tidying up some discarded restraints that were scattered around.

I cleared my throat tentatively, “Um, Mistress? I just wanted to say, I haven’t actually given you any money yet, and it feels like I’ve been here for a while.” She turned around and strode back over to me, sitting down in front of me.

I swallowed and then continued, “I just don’t want to go too far. Is the session over now that I’m not gagged anymore?”

Mistress Caitlin sighed and tutted, “Oh sweetie.” She reached forward and shoved the ball gag back into my mouth. She swiftly buckled it in place.

“MMmmpph!?!”

She smiled down at me, playing with my leash in her hand, “Did you really think I was letting you go after your session time? You never gave me any money, you’re right about that. That means this has all just been two adults playing with each other, and I’m not quite ready to stop playing.”

“MMMM!!”

“Oh no slave, I was serious before when I said I was going to keep you. You’ve got potential to be an excellent slave boy and I‘m going to train you until I’m satisfied. I usually charge submissives thousands of dollars for my full time slave program, but you get to experience it for free. I’m not training you for anyone else but me you little slut.” She swatted my behind and then clucked in concern as she saw the fear in my eyes.

“None of that now little one, it’s nothing to be scared of. You are owned now, you don’t need to worry about making any more decisions. All you need to concern yourself with is being the best slave you can be. I will take care of you and everything else that you once had to worry about.” She stroked my hooded head, running her fingers across the tightly strapped ball gag, “You just look adorable all restrained and gagged. My collar looks so good on you.” She tugged at the leash.

I began mmph’ing through my gag but she just shook her head, “You’re not going to get out of this slave. I’ve already made up my mind and prepared everything here for you. Oh, don’t get me wrong, you’ll still be paying me. But that will come later once you are fully broken to my collar, and understand that I also own your entire livelihood, not just your body. Now let’s get you settled in for the night.”

She led me by the leash back over to the main room, where I now saw a large cage in one of the corners. She undid the armbinder and swiftly placed a pair of bondage mittens on my hands, locking them in place and then connecting them with a short chain. My fingers were now curled into useless little balls, preventing me from even attempting to escape from my other bonds. I moaned dejectedly and she laughed again, “Finally sinking in that you’re mine? Good.”

She pushed me into the cage, still hooded, collared, and gagged. She slipped the blindfold back over my eyes, plunging me back into darkness.

“Sleep tight slave. Your training begins tomorrow. I hope you enjoyed your bondage session, because there’s going to be a lot more to come.” She walked away, chuckling to herself. What had I gotten myself into?