Sir Takes Lilly's Anal Virginity

Sir presses me forward against the spanking bench, "Into position."

His voice is more demanding than normal, and I can tell he's picking up on my reluctance. Our time together has been fantastic, making so many of many fantasies come true. But, tonight I'm scared.

Some things are better as just that, fantasy.

My knees find the edge of the bench and I drape myself over the firm leather. He grasps my wrist and firmly pulls it forward into the thick banded cuff near my face. He has to pull the cuff as tight as it will go to secure my thin wrist before moving to the other side to repeat the process. My breathing is already shallow and quick in anticipation of tonight's activities. We have been gearing up for this for some time, and finally, Sir says I am ready to lose my anal virginity. Me, I'm not so sure. Actually, I'm terrified.

"Spread your knees," his deep voice never fails to send my pulse racing. I try to shuffle my knees apart, difficult considering my position and the padded bench base they are resting on. He lets me struggle for a moment before grasping my bent leg and pulling it to the side, strapping down restraints over my thigh and then my calf. He repeats the process on the other side.

"Last one," he pulls a thick band across my lower back and just like that I'm completely immobile.

He kneels by my face, his tight thick abs and waistband of his boxers at eye level. Lowering his face to mine, I see sympathy in his eyes. "I know you're scared, but you want this. You need this."

I know he's right, even though my pulse ratchets up to a new level. His broad muscled shoulders and torso almost make me drool, despite my fear. Yes. I need this.

After playing for several weeks, we've come to an agreement of sorts. Tonight, there are no safe words. I trust him and he knows what I need. We've been playing with anal plugs, and I love it, but I want more. I desperately want him to take my ass and own me in that way. But his cock is so big. So thick. I can't manage more than a small plug without complaints and I know at this rate it will take forever to prepare. So, I've said fuck it. If I'm being honest, the thought of the pain turns me on. But I need to not have a choice or I won't be able to go through with this.

Sir's light touch along my spine makes me shiver. I can only see his feet as he approaches the toy wall. The not knowing is always the hardest part for me.

His foot falls slowly approach me, "Breathe, Lilly."

Then, there's the strike, making me gasp. It's the cane and I'm surprised. The biting pain across my ass makes me cry out immediately and I know there's already a welt. That one strike from the cane is enough to make me wonder if I was all wrong about what I wanted tonight to be. The fantasy is almost wiped away with that one bite of sharp pain. Doubt and fear crowd my mind as the next strike falls. It's lighter now, only eliciting a whimper from my slightly parted lips.

"Remember Lilly, I have the control. I will decide how much you suffer tonight." His meandering steps around me stop, "You're lucky I'm not a sadist, or else all this fear in the air would be making me crazy," he lets out a light hearted chuckle. "Relax, darling."

His laugh lightens the mood somewhat, but I still flinch in my restraints at the light touch of his fingers on my shoulder. His gentle caress, first along my shoulders, then down my back, feels like heaven. I wish I could lean into his touch; be engulfed by him.

The next fall of the cane bites, making me call out. I feel myself sinking into the pain, my natural craving for it coming out; my internal sense of competition to see how much I can take. Sir's hand soothes my reddened ass, he's kneeling behind me now. His hand dips to my pussy, finding me wet already.

"Your body likes pain, hm?" His finger slips inside of my swollen wetness, "Answer me." The timber of his voice gives me no choice but to answer, "Y-yes Sir."

"But my sweet Lilly gets so scared, so timid..." His palm cracks hard against my warm ass cheek making me suck in air, the finger still firmly inside of me. The firm spanks against my bottom continue, feeling extra rough on my cane reddened ass, but I'm relieved the cane is gone, and my confidence at being able to handle the scene returns.

My ass feels hot after the dozen or so swats, and then Sir is on his feet again, "I'm going to strike you four more times with the cane. I want you to count them."

I'm surprised for a moment; he's never asked me to count before. He's also never gone in this order before. Cane. Spanking. Cane. I don't know if I can take four more strikes of the cane...

Before I can contemplate this too much I feel the strike and cry out. I want to curse him, but instead I manage a whimpered, "One."

"Good girl," and those two words give me courage to continue.

The cane slides through the air, blistering pain, "Two."

There is nothing else now, just the pain and the need to not let him down.

"Three."

Only one more. I can do this.

The burning pain strikes the space between my upper thigh and the swell of my ass. I scream as my brain registers the shocking pain, a sound I'm not sure I've made before. With my gasping, ragged breath, I manage to whisper, "Four."

"Excellent baby, such a good girl. You took that so well," Sir's hand rubs my ass and thighs, caressing lightly. His hand brushes my hair away from my face and over my other shoulder.

"P-please, n-no more c-cane."

Sir lightly wipes my tears, "No more cane baby," he reassures me with light kisses. I let out a relieved sigh, my plea being just that.

I'm still recovering my senses, so when Sir is behind me again, I have no idea what's in store. I feel his hand at my pussy again, he's on his knees behind me. I feel something hard and foreign at the entrance to my cunt.

"Try to relax sweetheart," there's a pressure and stretching and I realize he's working a very large dildo into my pussy. It's a different pain then the cane, it's dull and aching this time as my body stretches and tries to accept it. It's well lubed and he's unrelenting as he works it deep inside of me. The width makes me feel I'm splitting in two, but that's nothing compared to the pain I feel at the length.

I cry out as the large phallus bottoms out against my cervix, "Agh, please, stop!"

"Shh, darling just another bit, you can take it," he tries to soothe me as I feel him corkscrew the large toy inside of me.

The pressure against my cervix hurts and makes me stomach feel sick, "Please," I manage to whine, "I can't." I'm trying to kick my feet out of the restraints as Sir's body weight presses against my lower back.

"I was going to be nice, but since you feel the need to complain this is only going to be worse for you."

I cry out and bite against my lip. Sir never gives warnings. He lets me speak until it displeases him, and then I pay the price.

With a firm, unrelenting hand, he presses the base of the toy all the way into me.

I manage not to scream, but I'm crying again, the deep pressure against my cervix making my abdomen cramp horribly. He holds it there, hard, "Count down from ten, slowly."

I struggle to control my crying so I can do as he says, "Ten," I wait a beat, "Nine, Eight," he doesn't stop me so I know I'm counting slowly enough. When I get to one my pussy almost feels numb from the aching, constant pain that seems to engulf my whole lower body. He loosens his hold on the dildo and slowly eases it out of my aching pussy. I close my eyes and gasp for air as I hear him walk away. I take the moment to try to compose myself but I'm only pain and the absence of pain at this point. There are no complete thoughts in my head.

"Here," Sir holds a tissue against my face, helping me blow my nose while restrained. He stays kneeling at my face, stroking my hair and cheek until my tears stop and my breathing is somewhat normal. This session has already felt like too much for me, and I know we aren't even at the main event.

"We're almost done, you can do it," he seems to read my mind.

Sir kneels behind me and I feel his hands on my soaking cunt. My body has produced copious fluids trying to endure the insertion of the massive toy.

"Relax darling, this isn't going to hurt," I feel Sir's hands on my pussy. First one finger enters me, slowly, and then two. So slow, so gentle. His other hand reaches around to my clit and he applies firm pressure. He strokes me like that until I'm bucking hard against him, crying out with my orgasm. I let my body melt into the leather bench, glad at not having to exert the effort to hold myself aloft.

I'm still shaking from my release as his soaked finger presses against my anus. After his ministrations up to this point, I'm completely exhausted and simply submit. I let his finger press into me, unable to tense or resist. One finger becomes two and I welcome the pressure. He scissors his fingers deep within me and I moan and tense slightly at the new feeling, "I know baby, you're doing so well." His two fingers saw in and out of me slowly and all too quickly they're gone.

Sir leans over my lax body and I feel his thick cock against me, "No plugs this time baby, you're just going to feel me, ok?"

I whimper, suddenly not sure if I'm ready, expecting more preparation.

"It's going to hurt, but I want you to accept this pain, just like you've done so well tonight, ok?"

"Yes Sir," I manage to whisper the words.

"Good girl," Sir grips my hip with one hand and his cock with the other.

The thick head of his cock feels impossibly huge against my tight entrance, and I know it's because it is. He's much much too big for me, and this is going to hurt. He has to push hard before my tight ring begins to open around him. The burning pain is making me pant, but my body can't resist the continuous pressure and after a moment the giant head of his cock is inside me.

"Argh," I cry out as he gains entrance. I feel like I'm going to tear or that I already have. It's burning and I'm crying, "Stop, stop, wait!"

"No baby, this is what you need," Sir is holding himself still over me, but not relenting. His voice perfectly steady and calm.

"I can't," my voice sounds like a wail as he presses deeper inside of me.

"Aghh, stop!" I'm desperately pulling against the restraints now, the burning, searing pain in my ass feeling like my body is being ripped apart. Sir doesn't withdraw but leans closer to my ear, "I'm not going to stop, so you need to try to relax and accept the pain that you're feeling."

I let myself collapse against the restraints and cry as the pain takes over. When Sir begins withdrawing I feel as if my insides are being dragged out of me along with his massive cock. The head pops out leaving me gaping and he takes the opportunity to pour more lube over and into my ass and on his cock. Again, the head splits me open and he presses forward making me cry out. The pain is somehow worse than what I thought, perhaps because Sir skipped the plug and any other toy this time, seemingly wanting to brand me with this torturous pain.

I keep waiting for some form of pleasure to take over, but it doesn't come. There is just burning, aching pain, deep in my body. Sir continues to saw in and out of my aching asshole as I murmur pleas and beg him to stop, that I can't take any more.

"Lilly," my name ensures he has my attention as he pauses his strokes, "I'm going to thrust into your asshole ten times, very hard and very deep. You don't need to count. And on the last stroke, I'm going to cum very deep inside of you," his cock begins it's slow retreat before the onslaught he has promised.

I can't form words, and he seems to know this, not demanding a response.

The first hard thrust makes me scream as I feel his balls and the wide base of his cock against me for the first time. He pauses for a moment before repeating the process. I can no longer scream, my body at the breaking point. I am just a world of pain as he attempts to split me open with his cock. I sob against the leather bench, hating him and begging that it be over. Finally, he's pressing himself into my depths, gripping both hips and I feel his cock thicken even more before the warm wetness bathes my insides. He let's himself relax against my back, my sobs racking my body.

"Ok baby," he pulls himself out of me, "It's over, it's all over." He quickly loosens all of the restraints and gently lifts me away from the bench, pulling me against his chest, "You did it, I'm so proud of you."

Sir wraps me in a warm blanket and carries me to his bed. When my tears finally stop the exhaustion takes over and I fall asleep, curled against Sir's chest.

When I wake, I'm laying on my stomach as Sir applies lotion to my aching body.

"Shh, it's ok, you're safe."

He sets the lotion aside, tipping my face up to meet his, "How are you feeling?"

I manage to nod my head, still feeling shaky and unstable.

"Use your words, sweetheart," his voice is gentle and soft.

"I'm ok," at least I think I am.

"Physically, you're perfectly fine, no damage. I made sure."

I realize I'm surprised, but although my body aches, nothing feels overly uncomfortable.

I let out a breath of relief, "Thank you."

"Any regrets?"

I think for a moment. I feel incredibly powerful... No, invincible, in this moment.

"Fuck no."