A Day of Firsts

by Caligula

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© Copyright 2019 - Caligula - Used by permission

Storycodes: F/m; D/s; femdom; leather; tease; denial; costume; maid; bond; gag; straitjacket; hood; oral; pegging; strapon; climax; cons; X

It was one of those rare nights when I actually sleep well. I knew from the night before today would be a special day and considering we had not done anything in the area of play in some time, I knew Domina had a major idea for me, I just did not realize at the time just what exactly it was. I normally sleep in my chastity cage, but last night, Domina neglected to put it on me. I really didn’t think anything of it at the time.

“Time to get up.” I heard her gentle voice coax me from my deep sleep. I noticed as I was stirring that a hand had caressed my then limp member into somewhat of an aroused state, coupled with the gentle nips on my ear lobe as Domina slowly made me wake up. Was that leather I felt? I was not sure, since I was still a bit groggy.

“We have some big plans today, you, I and this,” she said, referring to my growing friend, “but first, we have to get dressed.”

With that, she took my hand and helped me from bed. I sleep nude, as does she, but today she was already dressed as she got me out of bed. She had apparently awoken sometime before and was dressed in her full regalia of a black leather skirt, corset and boots, her elbow length opera gloves covered her hands. She was a vision in leather, but I knew there was something going on today that I would not soon forget.

“Go take a quick shower, and come back here. I want you nice and clean,” Domina told me, popping me on the behind as I went. Domina is not a cruel woman, just very impish when it comes to our play. It was agreed at the beginning of our relationship that discipline would not come from any sort of corporal punishment. I suffered real abuse at the hands of someone, and the idea of corporal punishment was something that I would rather not consider. Domina was very understanding when I had explained this to her. She cuddled me tightly and stroked my hair while I had quite the turret of cathartic release.

The hot water felt great cascading across my back and front. Since I stay shaved all the time, the water felt nice across my testicles and tumescent shaft, and a good bit of time was spent washing them, but I was careful not to get too excited. The last time I made that mistake was, let’s just say eventful and leave it at that.

Finishing quickly and toweling dry, I returned to the bedroom where she was waiting. I took proper position before her, head down on my knees.

“Very nice,” I heard her say to me as she walked around, “today you have some special tasks ahead of you. Perform well, and you will be rewarded. Fail, and you will be reprimanded for your actions. Do you understand?”

“Yes ma’am, I understand,” came my faint reply. I was on pins and needles, wondering what plans she had for me today.

“Good. Time to get ready.”

Domina took my hand, and I stood up. I did not know what all she had in mind to do, but I was quivering with anticipation over what plans she had. First, she had me step into what appeared to be a belt, but looking closer had an “O” ring attachment on one end, and underneath, what looked like a small dildo attached. I gulped. Domina had used a finger in me a few times and massaged my prostate as part of foreplay. We had never done anything to this degree. My swollen member rose with anticipation.

“Got to love the Internet!” I heard her cackle as she slid the ring over my testicles and shaft before settling it against my pubic bone.

“Bend over.” I complied and felt a warm hand caress my bud in the back. She slid one, then two and finally three fingers inside me, twisting and turning as I could feel the lube moisten my insides. I began to moan softly.

“I am glad you like that,” she whispered in my ear, “I thought you would like this little toy I found.” And with that, the dildo was pushed into my rear. I gasped slightly, feeling the pressure on my prostate and making my already full member swell even more. I reached to touch myself, but as I did, a hand slapped mine.

“No. You may not touch yourself.”

I whined a bit, but I knew this was for my own good. I loved to hate control like this.

After the plug was secured and Domina satisfied, she turned her attention to the rest of me. An outfit of latex lay on the bed, well powdered and ready to wear. She helped me into it, as I noticed it was not just any outfit, but a French maid uniform, complete with open holes where the nipples would be tugged through. Under the skirt went a pair of stockings that ran up to the thigh, and full length pair of matching gloves. Domina had spared nothing on this for me today.

Domina had not lacked for money. I was injured a few years back in an accident at work. The settlement with the insurance company was substantial enough that Domina did not have to work and could spend her days shopping for fetish wear, toys and plan for days like today.

The outfit snuggly fit, as if it were tailored to me specifically. “Just a few more things, and we will be done,” she pulled my chin up to meet her eyes as she said this, “I know you have fantasied about this for a long time, and today, it comes true.” As she spoke to me, she pulled me into her, tugging on my almost purple friend as she kissed me. I held my eyes closed, and as she pulled away from me, I left my mouth slightly agape. I felt something pushing in, so I instinctively opened my mouth the rest of the way. The penis gag slipped in with no effort. My eyes popped open. I started to grunt in protest, but I realized that discretion is the better part of valor. I sighed deeply, and Domina laughed ever so slightly before stepping behind me to cinch the gag down.

The straps were pulled more tightly across my face than in times past, and I winced slightly, but she buckled it down. She returned to my face, admiring her handy work. Meanwhile, she continued to stroke my fully engorged member. I remained ramrod straight, knowing better than to utter any sounds.

“Now, the final touch, or should I say, don’t touch,” she said, looking me in the eye with an almost evil look, “today, you will clean the house. It is filthy, and you need something to do. However, I do not want you getting out of hand, so I will be restricting your hands. Place your hands in front of you, crossed over.”

I complied, and Domina buckled a strap around my neck and secured my hands to a leather strap in front of me. My wrists were held tightly in front of me, and I could not move them except up and down, but even then, it was too little to make much difference. There was no way I could reach down to my penis or behind me to remove the gag. I was at her complete mercy.

With my mouth filled with gag, there would be no way I could escape, I grunted slightly in protest and tried to draw some sympathy with my eyes. I knew this was futile, but I always tried. Besides, Domina enjoyed my whimpering and discomfort, and I enjoyed sharing it with her.

“Aw, you uncomfortable?” Domina asked, “Whine if you want, but you will stay how you are until the house is clean. Whine too much, and you will get no release.”

I sighed through the gag in compliance, knowing there was not much else I could do. Domina placed a scrubbing brush in my hand, pointed in the direction of the shower and waited for me to start walking that way. I was lucky, she did not hinder my walking in anyway, so I could get around with relative ease. I set myself to cleaning the master bathroom.

The rest of the day was very much a blur. Every once and a while I would be working, and Domina would come up to me and tug on my penis, twist a nipple or something equally teasing. She would regularly wipe the lines of drool from my front and remove the gag for me to get a few drinks of water. Each time she said nothing, only checked on my safety and well being. She would then disappear to another part of the home while I went back to work.

Never once did she speak to me, or even look me in the eye for any reason. Each time got me more and more frustrated, and made it very difficult to concentrate on cleaning the house. I lost track of time, burying my head (literally, since my hands were against my chest) into my work. The entire time I was curious about what would happen at the end of the day. Eventually, the house was cleaned.

Late that day, I could tell because the sun had moved across the house, Domina came back to me.

“You have done well, my slave. It is time for your reward. I am going to remove your clothes, gag and plug. I want you again to shower and come back to the bedroom.”

I winced as the she took the plug out, and the cool air against my skin made me shiver slightly. I again took to the shower, enjoying it as much as I did before, but still curious what Domina had in mind for me now. When I returned to the bedroom, I almost collapsed from what she held before me.

I could not believe my eyes. I had long dreamed about straitjackets for years, but never thought I would have the opportunity to wear one, but in her hand, waiting for me, there was a beautiful black leather straitjacket.

I swallowed hard, trying to ignore the tremblings in my gut. Domina held the jacket up before me, waiting. I slid my arms into the jacket. Domina did not speak a word to me as she stepped around behind me, slowly pulling and buckling each one of the heavy buckles in the back. She worked her way up to the top of the jacket, pausing ever so slightly at the collar. She cinched it down.

Without a forethought, I lifted my arms and crossed them in front of me, shivering in anticipation at what was to come. Domina reached around me, guiding her hands across the leather arms to the back. She then lifted the two straps and tightened them down as well. I felt her arm cascade along the inside of my thigh as she reached up and grabbed the two straps from underneath. She buckled them in place before returning to my front.

By now, I am ready to burst, but again, Domina says nothing. She reaches between my arms and grabs a single strap. The strap goes over my arms and then pulled into a buckle above my groin. As she tightened this strap more tightly than the others, she ever so gently tapped the tip of my penis with the loose end of the strap. She then took my testicles in hand and squeezed ever so slightly.

I moaned into the gag, a slight, thin line of drool beginning to fall from the bottom.

“I see you like your present,” she finally spoke, releasing her hand, “I like this part the best.” Domina reached to my front, and lifted two flaps over my nipples. “See?” She then stepped out of my sight for a second before returning with a silver chain with two clamps at the ends. I knew immediately what they were.

Domina took one nipple into her thumb and forefinger, twisting the bud ever so gently. It sprang to life and was immediately rewarded with the clamp. She did the same thing with the other side. Before she was satisfied with her work, she tugged on the chain and let it fall down to my leather-covered chest.

I yelped into the gag. Domina said nothing. She took my penis in hand and stroked it until I stopped. She then disappeared behind me again.

I was plunged into darkness. A leather hood was pulled down over my face. The hood had a small opening for breathing and not much else. Domina then tightened the laces down until the bottom, tying them off. I heard a soft clicking noise. I realized the hood and straitjacket were now closed with a lock. I was completely at the mercy of Domina.

I started to struggle, testing my bonds and grunting in frustration. Domina reached down and again began to stroke me before helping me lie on the bed, face up. I could only imagine how I looked at this point. I heard Domina get up, as she did, she spoke, “I am going to go and relax on my own for a while. Don’t go anywhere.”

She left me there to my own devices. All I could do was thrash around and wait. It was maddening and wonderful at the same time.

I lay there for what felt like forever, when I felt Domina come lay back beside me on the bed again. I felt her hand caress the leather of the jacket and down my leg. I shivered, not knowing what plans she had for me now.

“Now darling, I know you have wanted this for a long time, but I was waiting for the right time to introduce you to it,” I heard her say through the muffling of the hood, “and it is almost time. I have been watching you all day work and you have made me very hot. It is almost time for your reward, but first, you must clean me.”

Domina climbed up on my chest and settled her face into mine. All I could do was wiggle. Domina unmounted me and giggled. “Whoops, forgot something.”

She then lifted my head and unlocked the hood and jacket combination. She lifted the hood up and off, then unbuckled the gag. She laid me back down as gently as she had lifted me.

She again climbed up on my chest, her glistening mound was in front of me, and I smiled. Domina lowered herself, and I began. Domina has three piercings – clitoral hood and inner labia. I made extra certain to give more than enough attention to each one of these as well as sucking on her rock hard clitoris. Meanwhile, Domina was reaching behind herself, grabbing the chain between my nipples and using it to gauge the speed of my tongue and mouth.

My hard work was appropriately rewarded. It started as a slight shiver and low hum. Then Domina thrashed against my face, pulled hard on the chain and let out a sound that made me glad to live in a remote area. Her thundering orgasm was only a delicious part of my entire experience so far. Domina settled back on my chest for a few minutes to compose herself. My face wet with her juices.

Domina got up and walked out of the room for a moment. She returned with a warm, wet cloth. She helped me sit up again, cleaned my face off and smiled. She made certain I could sit up and put a blindfold around my eyes. She let me back down and got up off the bed.

She was again gone for a few minutes, but I could hear her stirring around the bedroom. I could only imagine what she was doing, and I found myself thrusting my hips into the air. I heard her giggle as I did.

Domina began to speak, “today, my slave, you have learned all about what you have wished for many times in the past. I know what you look at on the Internet, I know what interests you have but have been extremely scared to share with me for whatever reason. Now, I am breaking down those walls. Open your mouth.”

Confused, I complied. A hard, rubber penis filled my mouth and Domina began working it in and out of my mouth. “Get this good and wet for me, my slave, for soon you will be feeling it inside of you.”

That was all it took, I doubled my efforts, twisting my tongue over Domina’s she-cock, trying to deep throat it without gagging. When she took it away, I leaned out, trying to take it back into my mouth. All I could do was whimper out a, “please.”

“Like that do you? Good. One day you may get a real one to try out.” I heard her say as a ring gag was pushed in my open mouth and buckled in the back. I touched the rim with my tongue. Domina stuck her fingers in my mouth, allowing me to lick her leather covered fingers for a moment.

“It is time for your reward, my slave. I know you have wanted this for a long time, and it is time. You will be taken from behind and if you are good, you may get release. Roll over onto your stomach, and pull yourself up.”

It took a bit of effort, but I did as told, Domina helped me some, until I was rolled over, my rear in the air. I wiggled a bit, getting myself comfortable. I was beside myself with excitement. I was finally going to get pegged.

I have long wanted to try this. I never could get the nerve up to ask. I always meticulously cleared the browsing history, but apparently Domina had a key logger on the computer.

Domina reached under me, and toyed again with my swollen testicles and penis. She fondled them gently, drawing my attention away from other things, until I felt something push against my rear. She had started to penetrate me at last.

I had worn plugs before, and some vibrating, but the sensation was nothing compared to what was happening now. It was a slow, rhythmic feel, like a long walk on a Sunday afternoon, and I was in heaven. Infrequently, Domina would slide her hand back to my penis, testicles and nipples, toying with them just to remind me who was in charge before taking hold to the straps that ran up my crotch, holding them to get better depth.

I could barely hear what she said next I was so caught up in the moment, “I know you are loving this, my slave, but there is one more surprise I have been waiting to give you. This lovely feeling you are getting has an additional surprise. Ready yourself.”

I took a deep breath, drool poured from my stuck open mouth as it happened. From somewhere, I do not know where, Domina turned the dildo on full blast. It rattled my insides with sensations.

I could not stand it much longer. Domina sensed this and removed her hands from my penis. She concentrated instead on holding the straps around my crotch, thrusting the dildo deeper within me. She picked up the speed, with rhythmic movement until she was pounding my rear. I could hear the crescendo of her own orgasm building up as she screamed herself, burying the dildo deep within me.

That was it.

I came, harder than I ever had in my life. I screamed into the gag, drool flew from my lips and face and I contorted violently, shaking myself on the rigid pole buried within my guts. The arms of the straitjacket kept me from moving too much, but my hips were quivering like cold gelatin.

I was heaving for breath afterwards, and Domina collapsed across my back. We lay there a few minutes, the two joined from behind. We said nothing.

Ever so gently, Domina withdrew herself and quickly ran to the bathroom to remove the strap on and harness. She returned to me, and I winced as the clamps came off, and my jaw was sore from the gag, but it was pale in comparison to the euphoria I was experiencing. I continued to have aftershocks.

Domina helped me stand as I was on shaky legs. She unbuckled me from the straitjacket, helping me take it off slowly, as I still was in heaven over the delight of having a straitjacket at last. Domina too, undressed, for she was tired from wearing her full Domina outfit all day. She stepped into the kitchen for a glass of water. She took a large gulp and offered me the remainder. I drained the cup before setting it down.

We lay back down on the bed. “Well, my slave, did you enjoy that?” Domina asked me, as she stroked life back into my nipples. Still on endorphins, I mumbled how much I did, and nestled myself into her arms,still trembling from the aftershocks of a thundering orgasm.

“I am very glad that you did.” I heard her say as I was drifting off to sleep, “I enjoyed that myself. So much in fact I think you may clean the house like that all the time from now own.”

I smiled, and Domina kissed me gently before pulling the covers up and over us both. I told her good night and drifted off, still lying in Domina’s embrace.

For the life of me, I swear she said something about doing yard work tomorrow in the same fashion as the house work…

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