First Time Strap-on with Mistress

I lay naked face down on the floor as my nipple clamps were beginning to bite. I could hear a rummaging as my Mistress searched out of my sight.

"I'm just looking for something for you to ride," she muttered, deliberately teasing. I remembered what I had put in my e-mail but was she really going to go through with it? Earlier I was surprised to go outside and for her to fulfil my first fantasy, but surely the next thing I asked for was going beyond her remit.

It was as if there was a refusal to believe that these fantasies could come true even though Mistress did nothing to hide her agenda. It wasn't until I was struck on my buttocks for being late that I really believed I would be punished. It was not until I was naked outdoors did I think that would happen, despite being on a lead indoors going through countless doggie commands.

The denial going through my head was absolute, and even when Mistress said,

"I'm looking for something for you to ride", I still didn't believe what I was in for.

"Turn over she ordered, and I obeyed the long nipple clamps catching on the floor and whipping around on release as my body turned. I lay on my back, looked up, and caught sight of myself in an overhead mirror.

Yes, it was me. I had finally submitted whole-heartedly to a mistress and was awaiting more torments. I was in a dream. I congratulated myself for making it to the world of my fantasies but was she really going to shaft me?

I looked to the side, still not daring to believe, and I saw Mistress with a large pink tapered strap-on protruding from her crotch. I swallowed hard as she expertly rolled on a condom along its entire length. I began to worry a little; the strap-on was at least eight inches long, and when a man is going to be on the receiving end of a phallus, you don't exaggerate.

Mistress strolled casually towards me, stroking her cock slowly to tease or torture me mentally or professionally, ironing out any air bubbles. She stood upright between my legs.

"All of our strap-ons are cleaned thoroughly," she announced to ally any fears. I did feel better for that information, but with it came the realization that I really was going to get shafted!

"First, I want you to suck my cock!" she stated with relish and knelt to my side, her knees in-between my arm and torso.

I wondered how she was going to take me? Was she going to do me missionary style where I was laying? Or get me to pull my legs up so I would be in the diaper position or have me on all fours and have me doggie style? There was a bondage table waiting menacingly in the corner of the room, and I thought she would take me there rather than join me on the floor.

She offered her cock to me, and I would do my best to please her for the time being. I didn't mind being humiliated, that didn't hurt, and as long as her cock was in my mouth, it wasn't going to be doing damage elsewhere.

"Suck it!" she commanded with authority, and I quickly lifted my head to clamp my mouth on her strap-on.

I sucked quickly, noticing the latex sheath on my tongue. As my head motioned back and forth, my teeth lightly chattered on her cock. I forced my jaw to open wider, not wanting to puncture the condom.

"Lick it!" she demanded, and I instantly disengaged my mouth and went to sliding my tongue along the length.

"Suck it!" she quickly revised, and once again, her cock was in my mouth, slowly fucking away with tiny thrusts.

Again the will to please her took over, so I took as much of her pink strap-on down my throat as possible.

"Good boy", she praised, genuinely pleased with my efforts as I quickly worked up the length. I started to gag and was instructed promptly by Mistress.

"Slowly, take it slowly", withdrawing kindly and offering the tip for me to work on.

"Now, what am I going to do to you?" she questioned teasingly. The game was up. I could kid myself no longer. The time for modesty and pride had passed, and I was left with the truth.

"You're going to fuck me!" I heard myself say.

"Yes, that's right!" she delightfully giggled. She sounded as if she was enjoying herself.

"Wait a minute, would you mind if I filmed this?" she eagerly asked, breaking character.

"Of course not", I heard myself say, "as long as you film my good side". Mistress burst into a fit of giggles once more, which I found very endearing.

"Are you going to take my virginity?" I jokingly asked, causing her to laugh harder.

"I'm afraid so", she managed to emit before laughing again. It was nice to please her, but I felt I was crossing the line of the master-servant pact and apologized.

Mistress sprang up and rushed to get her camera out, her pink strap-on flopping from side to side. She returned and knelt beside me and once more offered her cock.

"Now suck it!" she demanded with menace returning to her character, and I eagerly obliged once more, clamping my mouth on her phallic tip.

"Lick it!" and as soon as I redirected my mouth, she reverted to wanting me to suck.

"Suck it," she ordered. I found it interesting that the timing of her commands was almost identical to the first time.

"Right, what am I going to do to you? she repeated this time for the camera.

I let the strap--on fall out of my mouth and answered, "You're going to fuck me," I repeated before returning to my oral order.

"Oh yes, I am", she giggled, her voice delightfully rising an octave over the short sentence.

"Thank you, mistress", and with that, she fucked my face, pushing her cock into my cheeks before trying to make me gag as she forced its almost pointed tip down my throat. This time I took it slower. I wanted to impress her with something, even if it was just sucking a model cock.

"Good boy", she animatedly congratulated as if talking to her dog. She jumped up and put her camera to one side. She then grabbed a big bottle of lube and stood dominantly before me as she ran the lube along her prosthetic shaft.

I was still at a loss. How was she going to take me? I still couldn't believe she was going to remain faithful to my e-mail. I remember adding in the scenario just to fill out the e-mail as a backup if my requested outside doggie play wasn't possible. In her reply, I was surprised when she said,

"Your fantasy made me smile with wicked delight", but then I bet she said that to all the boys!

"Now, let's get you fucked!" Mistress declared harshly as a penal sentence. Her words went right through me as I looked on apprehensively. The strap-on was large, too large for my liking, and it was a bit worrying, as I'd have never taken something like that in my back passage. I had done the exploratory feel with a finger and a little implement, but nothing that big. I started thinking about asking Mistress if I could try something smaller as I was, in effect, an anal virgin.

My thoughts must have registered on my face as she soon queried what I was thinking.

"What's the matter? Do you think it's too big for you?"

"Err, yes, to be honest."

Mistress stopped in thought for a while and slowly looked around the dungeon only to break and look at me.

"Oh come on, do it for me," she asked nicely and straight away,

I answered, "Okay," without any reservation or thought.

It was a strange power she had over me. I would do anything at her behest. This new phenomenon of wanting to please someone by letting her hurt and humiliate me was shockingly extraordinary. I had read about it so many times before, how an enslaved person would like to please his Mistress. To me, it all came over as phoney, play-acting, but now I was under the same spell doing anything but acting. I really did want to please her, and it wasn't very comforting to think how far she could take me.

"On your knees," she commanded, and immediately I obeyed. I remembered to put my hands behind my back and make sure I was upright in compliance with an earlier order. To my surprise, she lay down beside me, her pink phallus pointing ominously, rigid and perpendicular to the floor. She reached for a transparent plastic container and put it right up to my eyes.

"Lube," she stoutly informed and proceeded to pump the transparent liquid gel into her hand and then run it up and down her phallus with erotic intent.

Mistress was going to take me just as I had written, and I still had trouble believing my fantasy was going to come true. The electrodes that Mistress had attached to my testicles and had me dancing to her electric administrations earlier were still attached, as were the nipple clamps.

I swallowed hard and committed myself to my folly.

"Can I have some of that, please?" breaking the code yet again.

Mistress presented the lube to me without hesitation. I took the bottle and thanked her as she carried on spreading her liquid on her mast. For a brief time, the master-servant element of the scene had gone, and we were like two ordinary lovers going about our pre-love making precautions. It felt strange, as suddenly it had become very intimate. A massive transformation from the strict orders I had previously been put through.

I squirted a huge amount of lube into my hand. The little literature I had read about anal play had always stressed lots of lube and then more lube. I filled my hand to overflowing in one and pulled my bottom cheeks apart as far as possible. I lubed my ass, making sure to smoother my buttonhole as best I could.

Mistress watched as I prepared myself to be taken. A wave of humiliation flowed over me, as I felt belittled and unmanly, as I was about to endure the most prominent action of gender reversal possible.

My penis counted for nothing in this act, and it seemed to wither even more knowing this.

"Hop on then," she smiled mischievously, holding her cock at the base, ready to skewer my virgin ass. I straddled Mistress at hip level feeling it was a little too impertinent to be right over her breast.

I grabbed the tip of the strap-on and guided it to my centre, and when I felt the coldness of the lube on my A hole I plunged down quickly. The cock pierced my ass a good three inches before I felt resistance.

"Go slow," Mistress whispered caringly, and I slowly let my legs lower myself down. The phallus bent in my ass. I must have been at an awkward angle, making penetration harder, but I carried on.

"It would be easier if your knees were under my armpits," Mistress caringly instructed.

I raised myself to my knees and felt the cock whip out.

"Move up here," Mistress instructed sensitively, and now having been given permission, I felt easier at being so close to Mistress.

My knees shuffled forward. They were sore and bleeding from the doggie exercise along with my toes. Also, my arms were still weak from an hour's worth of crawling at my Mistress's behest.

"Let me guide it in", she ordered with a whisper, and I was only too willing to let her take over. Her hands moved under my testicles and felt around my anus. She spread my cheeks with one hand and speared the cock up me with the other.

The cock slid up me with ease for the first five inches, and soon I began to groan.

"Slowly," Mistress whispered. She held my buttocks, half supporting to reassure a slow descent, helping me take it to the hilt.

I was looking right down at her face, her eyes concentrating on getting me skewered. I could not help but admire her cleavage once more. Wonderful breasts squeezed up tightly in her catsuit.

She quickly looked up as my lowering slowed. Her cock almost split me in two as I felt the spike go up to my stomach. I breathed heavily.

"Let yourself stretch around it," Mistress seductively whispered.

Usually, the girl asked me to wait while they stretched around my erection, but not today. I was waiting to be 'ready', and Mistress was very generous, making sure she didn't start to fuck me painfully from the start.

There was a strange closeness between us, one that I had never encountered before. The only different thing was I was taking the penis. However, despite her being a Mistress, there was still that comforting maternal female presence. A presence I was eternally grateful for as she parted my ass.

My legs were aching as I still had not taken the full eight inches, and my helping arms were close to collapsing.

I decided to plummet the last half-inch, letting my total body weight go. I did not take into account that the strap--on tapered out cruelly right at the base and suddenly stretched me open an extra half-inch. I cried out in anguish at the ceiling, looking straight into a mirror.

"Right, let's move," she suddenly ordered, bucking her hips up, making me even more aware of the spike embedded in me.

I pushed up on my sore knees fucking myself lightly on the shaft, modulating only an inch.

"Come on, you can do better than that," She scolded; "Fuck yourself." Mistress was back in character with a vengeance.

I did as I was told and pushed my body as high as possible without the strap-on popping out of my ass before quickly dropping down on her groin. I pushed up again on my sore knees and aching legs and let myself fall again, and then I got a rhythm going up-down, up-down. I groaned all the time through the brutal penetration searing through my ass and the ache of my limbs. I pushed up and down, but my arms were too weak, and my legs were close to giving out.

"Come on fuck yourself," Mistress urged.

And on command, I pounded up and down my legs and arms, extremely tired. I looked down at Mistress's face. Amazingly she was sighing with sexual pleasure. Surly Mistress was acting, I thought; although she was so good at role play, I would never know.

I broke into a sweat and gasped heavily for breath as I slowly came to an exhausted stop.

"Come on!" she once more forcefully commanded, flexing her hips rapidly, fucking my ass quickly.

I groaned again and slowly pulled myself up the pole embedded in me. I saw Mistress reach for the electric box she had used earlier to punish my balls. Mistress pushed for a shock, and I moved, but there was no shock to my surprise. One of the pads had detached itself from my testes, breaking a circuit. Mistress Soon realized this and gingerly tried to slap the pad back on, scared of being shocked herself.

I took this moment to take a breather, even though it was through the slight tender sickness of having my tight testicles slapped. As Mistress slapped my gonads with the electric pad, I became aware that sweat was now flooding down my back.

Mistress noticed the electric box was ineffectual and pulled hard on my nipple clamps instead. When Mistress pulled them, my sore nipples burnt into flame. I yelled again.

"I didn't say you could stop," she admonished, and once more, I slowly pushed myself up her invading phallus. My muscles were shot, and I could barely move.

My breathing had become rapid, and I strained to push my body upwards, slowly rising to the tip, at which point I would fall down heavily upon the spike shooting right up into me.

Mistress was relentless, "Come on!" she ordered impatiently "faster! Screw yourself faster!" I tried my very best to please her pushing my spread ass up as fast as possible, my legs and arms trembling with effort, my face grimacing as I slavishly pushed myself on. Time and time again, this happened, letting my body fall hard down onto her strap-on. Squealing lowly as the phallus split me, taking a few seconds to rest gulping in the air, before steeling myself to climb her mast once again.

Mistress could see I was trying my best, but it wasn't good enough. She grabbed my nipple clamps and pulled them upwards, trying to speed up my assent. Despite the pain that fanned out from my twisted nipples, I could move no faster. I reached the top of her cock again and wanted to fall, but Mistress Leyla cruelly held me up by my nipples. I tried to stay at her demanded height, but my legs gave out. I plummeted down, and yet again, I cried louder from the demonic invasion and the additional nipple stretching.

"Get off and turn around", she instructed, and I lazily pulled my ass off her strap on.

"Move!" she yelled, slapping my ass cheek for urgency. I took what little time it took to breathe hard and oxygenate my weary limbs, resting them as much as possible. It was that desperate.

I lumbered around, spinning on my sore bleeding knees, and once more straddled Mistress reverse cowgirl style, breathing hard. I backed onto the strap-on. It slipped in quickly, and I soon dropped on it ass first as my legs gave out. Unfortunately, it opened me up a different way, causing me to cry out as once more, the flared flange of the strap-on spread me unaware.

"Now fuck yourself," she continued to demand, slapping my ass again. I bounced once more with a bit of zest from the small rest my limbs were given, but after only five shafts, my airless limbs fell again. I flopped forward, gasping for breath, sweating profusely with her strap-on still deeply embedded. I looked down wearily at her leather booted legs which somehow began to move with her hip thrusts as Mistress took it upon herself to fuck me with fast short strokes.

I took the short quick strokes with gritted teeth and waited until she had burnt herself out.

I took a massive gulp of air as soon as her vibrato fucking had stopped. There was no time to rest, though Mistress quickly urged me on.

"Come on! Fuck yourself," she demanded, slapping my ass cheeks. My legs and arms were exhausted, and I had to use different muscles to obey her. I fucked myself by arching my back to and fro while pushing back on all fours, rocking on my raw knees and elbows.

I heard a rustling behind while I used my back muscles to flex on her cock. I was breathing heavily, plainly close to complete collapse. I rocked on all fours and flexed my back to its full to satisfy Mistress.

Suddenly there was a crack! I cried out as my balls seemed to light up and expand. Mistress had zapped me with an electric fork. I straightened my back and yelled at the ceiling as the electric current danced through my orbs. I fell forward as the shock elapsed, and I breathed deeply to regain some composure. The pain was excruciating but in a strange way, a relief for as long as Mistress was busy zapping my balls, there was a small rest for my limbs and ploughed ass.

It was that desperate, the merest of seconds of rest for my limbs, taken while my testicles were painfully zapped.

"Come on, or I'll shock your balls!" she yelled as I wearily started to fuck myself again. My body was so wrapped in the sensation that I had little ability to think, but Mistress's last comment did spark a thought. "I'll shock your balls," she said, but I was sure she just had.

The shock seemed bang on my testicles, but I was too weary to ask. Still, I did get the implication that the next electric shock would be fiercer, which was frightening as my balls felt close to exploding. Whatever was in store for me was out of my hands as the energy in my body was so low that Mistress could do anything she pleased.

My back now began to ache as my elbows were sore from rocking. I breathed heavily and flexed my back in broken, exhausted pushes along her cock.

"I'll have you up on there!" Mistress threatened.

I looked to where she meant and saw a bondage table. "Would that be so bad? I wondered as the sweat now began to stream down my face.

"Why was I taking this?" A question that was never asked. I could have just said no and drawn a halt to this agony, but yet that thought never crossed my mind. Instead, I just obeyed and pushed my body on, trying desperately to screw myself to my Mistress's content.

"Why was I putting myself through this hell? Why didn't I stop? Somehow she had possessed me. It was incredible, for the only conceivable way of escaping this never-ending torture was to endure all she commanded of me.