A text appeared on my phone: “You have some nervous messaging me again boy”.
I had contacted mistress online some time ago but lacked the courage to go through with the meeting, she was very unimpressed…
She was a mature mistress of around 40 and was in search of an “inexperienced and innocent plaything” and I had decided I would be a suitable candidate. She had outlined that she was very kinky, dominant and not necessarily looking for sex but a subject, a toy to command and play with. Being a young heterosexual guy but very openminded to new experiences I put myself forward. I had met with a dominant tgirl before despite still being quite inexperienced, however, I knew this time would be different. She was older than anyone I would typically meet and nevertheless with that came experience but it was her enthusiastic interest in kink which both excited and scared me the most.
I had arranged to meet with her previously but to her fury, I bottled the meeting. I don’t think this is uncommon when having experiences outside your comfort zone, levels of confidence navigated by how horny you are at any one time. At times I would be incredibly aroused by the prospect and at others ashamed. However, after my first failure, I found myself alone, to my own devices and excited at the idea. I messaged mistress again…
At first, as you can guess, she was angry but eventually, she was willing to give me another chance. Nevertheless, she made it very clear there would be no messing around this time. She told me she expected me in a certain location near her place by 4:30 pm and if I was serious I would be there and phone her at his time to follow her instructions. I agreed to her terms and apologised again for my previous performance. The reality of what was happening instantly started to hit me as it had before; plans were now arranged and this time I would see them through. As I left, the familiar nerves were hitting me hard, I hardly knew anything aboutmy mysterious Mistress, she had given me an idea of her interests and I had seen a couple of vacuum pictures. In both, she looked feminine and commanding in high heels and a tight dress but in reality, I still didn’t know what to expect of her. These nerves continued right up until my arrival at the road she had requested that I be. It was 4:20 pm and I was early, determined not to disappoint. I loitered for 10 painfully long minutes and once they had crawled past I took out my phone, went to her contact and took a big gulp as the phone started to ring.
Surely enough she picked up the phone, my nervous “hello” was met with a refined, feminine voice. She asked me about what I could see and impressed that I had kept to my word she continued with the next set of instructions. Following her orders, I walked down the street, Found her apartment block, rang her buzzer and made my way up to the correct floor followed by room in which I would spend the next few hours. I now stand outsidein nervous anticipation and what was to come after I would knock the door was now frightfully real, no longer mere online chat. I put my instinct aside and struck the door three times and almost in an instant, I was met by a tall, mature but feminine trans mistress. She had long black flowing hair, precise makeup and stood confidently in black high heels, stockings and a corset. She stood around six foot in heels and looked sexy, without being overly revealing.
I was beckoned inside and I followed her through her apartment into a small room. She told me to sit on a small chair and then left the room coming back with a drink to “help me relax”. Next, she took a seat on a taller chair looked over me.
“So you’ve finally found the courage to visit me” she finally spoke in a soft but authoritative voice.
“Yes miss, sorry about before” I apologised.
“Are you sure you want to do this?” she questioned intently and I nodded my head.
“Good boy, now I want you to finwas your drink and undress” she commanded.
On her command, I instantly finished my drink, removed each of my pieces of clothing and placed them in a neighbor pile on my chair while mistress looked over me. Scrutinising my now nude body she gave a hand signal which I followed, spinning around assuring she could see all of me. “Not bad slave” she began to complement, “however, perhaps you could afford to lose a few pounds”. As I thanked her, her hands inspected by semi-erect cock, “getting excited are we slave?” she questioned, that won’t be a problem” Next, she rose from her seat and produced several items from a draw. The first of which was a heavy, metal chatity cage. I had seen them in porn but never in person, I was immediately being told I was to lock myself away and I followed her instructions. I placed the tight metal ring first over my balls, preceded by my semi-erect cock which was not cooperating. Once finally through, a metal cage enclosed my penis and locked into the ring, keeping me trapped. Satisfied, mistress produced the second item, a collar which was tied quickly and tightly around my neck. Happy, she pulled it to the floor and I followed. Sitting back in her chair she ordered me to clean her high heels thoroughly, my tongue lapping at the black shiny material followed by the base of her slim stocking clad legs.
In moments I had been transformed into a slave. As I licked on All fours I could feel the weight of my cage pulling my manhood down, only reinforcing the reality that I was not in control. Bored of my effort mistress pulled me to my feet. “How sensitive are your nipples, boy” she questioned? I didn’t understand or know what to say, it was something I had never considered. “We will find out then” she accepted. Her question became clear as she produced a set of silver, metal nipple clamps connected together by a chain; expertly she adjusted them before clamping them tightly over me. I let out a groan of pain which both excited andhurt me and she laughed, pleased; these would be continuously tightened. Lastly, she produced a black hooded mask which was placed overhead allowing freedom only for my mouth. I was now unable to see, caged, collared and clamped. The sight of me must have been laughable, a grown man humiliated, turned into a toy.
“My my, look at you now slave, think its time to start your training” she chuckled gleefully. Clumsily, without sight I staggered into the next room, being guided forcedly by my collar. Next, I was taken to a low bed designed for torque which I fell forward onto. I was commanded to sit on all fours with my head to the ground, face down, ass up and I felt incredibly vulnerable. All of me was on show, but unsatisfied mistress had a request. “Spread your cheeses apart slave, mistress Wants to see your little pussy”. Agreeably I did so, my ass raised high and with help from my hands, I widely exposed my hole. “Tut, tut, tut, this won’t do at all!” she exceled disappointingly. Mistress was unhappy with the presence of any hair around this area and would not put up with it. “I’m going to have to fix this, slut, your pussy must be smooth before we start your training!”
Mistress left the room for a few moments leaving me on all fours, awaiting her return. The first thing she did was yank my arms backwards causing me to fall stupidly onto my masked face. Quickly, she cuffed my hands tightly behind my back, my vulnerable body becoming even more useful. Unable to support myself my body was positioned downwards, my head and shoulders propping up my torso but my knees remained bent so my ass remained presented to mistresses attention. I heard a swishing sound of water from behind me and sure enough, mistress started the process of making my “pussy” as feminine as she pleased. Warm water, followed by shaving cream was wiped delicately over my ass before she got to work clinically removing every last piece of hair. Once satisfied mistress patted me dry and smoothed excessive amounts of cream over me. I could not believe how smooth I had been made, her hands slip effortlessly over my cheeks and around my hole. I was smoother and silkier than most of the girls I had ever been with! The feminine smell of the cream also adding to the humiliation, I had given up my masculinity. Pleased with her work she finally spoke, “wow sub, now that is a real pussy” as she continued to run Her hands over me testing her work. A hard spank indicated she had finished the job and mistress was now ready to test her new plaything.
My training had now begun as mistress introduced a large amount of lubricant over my tight hole. I had had some experience with anal but still little and this was an extreme situation from me. After first teasing around my now smooth pussy, she eventually applied more and more pressure until my hole gave away and was intruded by an index finger. I gasped as I clenched around it. “This will be much easier for you if you relax”she advised knownly and as I eventually let go, she made her way into me with more ease, deeper and now with two fingers. Expertly, she slide her fingers in and out stimulating my prostate and I groaned. There was some pain but it also a lot of pleasure, disappoint edged with deep stimulation. Mistress had now moved me onto my back, legs overhead and when it got too much I felt a warm liquid seeing from my tortured, caged cock onto my stomach. It wasn’t a usual ejaculation and I didn’t think it possible but mistress had caused me to in some way to cum, milking my prostate gland, but she wasn’t done.
Pleased with my progress she told me I had done well and I was ready for the next level. Removing her fingers I felt an emptiness but this wasn’t to last long, she smoothed greater amounts of lube and before I knew it a Larger object was attempting to enter me. Painfully, it slipped into my tired pussy and I could now hear pumps of air from below me. What felt like a butt plug wasgrowing inside me, opening outward pushing the walls and rim of ass wider than they had ever been before. She pumped and pumped until she could sense my disappoint and then stopped. “Now we’re going to open up your pussy slave” she dictated, “when you get used to the feeling you are to tell me and It will grow larger until I am satisfied with your effort”. After a time it had been decided that I had deserved to be released from my cage and while the large intruder sat inside me she played, toying with my cock and balls, however, I was forbidden to cum. This process of edge me while continuously pushing the limits of my pussy continued for about 40 mins now and my stretched hole long for a break and being on the edge I long for relief.
Mistress was now satisfied with my anal achievement but if I wanted to finally cum and be released I had to endure another task. “Anything Miss” I exclaimed naively. I hadn’t seen daylight for over an hour now and was ready for the experienceto come to an end. First, she began to remove the swollen plug from my pussy, it was painful but as she pulled my muscles loosened their grip and it finally escaped my hole. My body tried to adjust to the new colossal feeling of emptiness, the plug had been in for so long that now I felt strange without the unnatural intrusion. I was then yanked to my feet and bent over, hands on the bed. I was unsure what was going to happen next, I had told mistress I wasn’t interested in sex but still, I feared the worst. Suddenly with a great “smack” Mistress’s hand swooped down spanking me hard on my delicious smooth cheeses.
“Arh!” I shouted, surprised by the assault.
“Smack…smack…smack” she continued as my ass becomes increasingly raw. Mistress, now bored changed different instruments using floggers and canes but I could Only guess the sight of her tools by the pain inflicted. Once finished she stood me up straight, “very impressive my sissy, looks like you can take a beating as well as your little pussy” she teased.
The compliments were lost on me, the meeting had been exciting but by now I felt it had run its course. Mistress, began to play with my cock and balls again and I felt I had finally earned my reward but as she played I could feel a tightening around my balls. Still unable to resist, rope enclosed around by scrotum putting huge pressure on my testicles, she started to tap and flick them menacingly causing me to wince. “Very good, boy” she excaimed, but unhappy with my reaction a slap was certain to provoke me and I screamed out while mistress laughed. Harsh pain was being inflicted while she simply managed to keep me hard, struggling my cock. After more torque, mistress squeezed my supplies and sensitive balls while struggling me faster and harder than ever, the feeling so incredibly intense that I eventually blew my load explosively onto the bed and floor.
Now I was allowed to leave.
Mistress released my arms, removed my collar and next removed my nipple clamps. As each clamp was removed I let out a “yelp”. The pain, once they were moved, was excruciating and mistress had certainly succeeded in making my nipples sensitive. Lastly, my hood was removed and the light seared my eyes, I hadn’t seen for hours and in front of me sat my mistress as she had at the start of the session. We exchanged a few words but I promptly dressed and then left.
Now at home I smoked a cigarette and tried to calm down, my thoughts raced about the meeting. I felt ashamed and guilty about being used as a toy and even before the meeting, I knew I would. The excitement had now subsided, however, I knew eventually the excitement would return again as it always had to make me consider another adventure. Undressing, I headed to the shower, cleaning the remainder of the cum, lube and lotion from my body. As the warm water cascaded down me, my ass stung from my punishment. Scrubbing myself deeply I feel how silky smooth my hole was once again,both the smoothness of my pussy and the ache of my ass and balls a reminder of what I had endured this evening.
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