A Day For Firsts

The day had finally arrived, the day that I had been looking forward to for so long. Today... was the day I was going to lose my virginity! And, as the ache in my dick reminded me, it was the day my Mistress would free me from this cage.

It had been a month since the unmarked box had appeared on my doorstep, a gift from my partner (and Mistress!) Elise for the wait until she could visit me for the first time. Of course, I was expecting a fleshlight or some other fun toy, but as I pulled the item out of the box, I recognised the curved metal and leather base from a thousand fantasies. I almost squealed with excitement just at the sight, barely waiting to slip the restraint around my cock and balls. There was a padlock in the bottom of the box, already unlocked.. Knowing the key was safely around Mistress' neck, I snapped it through the loops at the base, completing my captivity. She was so turned on when I told her, she masturbated right there with me on the phone! It was fucking agony and I loved it. All month, she would tease me and turn me on between all the sickeningly sweet messages people in long distance relationships send each other.

My thoughts were interrupted by the sound of rapping knuckles on my front door. It was her, she was here! I stepped to the door quickly and opened it, gasping as I saw Elise for the first time in person. It was one thing to see someone through a computer screen, but she was...

She laughed softly, noticing my awestruck stare. "You know how to make a girl feel welcome, Will."

I blushed, already on the back foot. Sheepishly, I stepped aside and let her into the house. She placed her luggage down by the door before she wrapped her arms around my neck and stared deep into my eyes.

"Have you been a good little slave, Will?" One of her arms disentangled from my neck, sending her hand straight to my crotch. Judging by the cooing, she was pleased with what she found. "So obedient! I am glad that you managed to survive the month without resorting to bolt cutters."

"Well all that torture makes our time together more fun, no?" I beamed with the praise.

"Absolutely, at least for me." She smirked and gave me a warm, affectionate kiss. I responded in kind, all of the affection left unexpressed flowing freely into her lips. We collapsed onto the couch. Sitting atop me and pulling back from the kiss, Elise wiggled her hips against mine, her ass pressed against the steel cage. She regarded me with an affectionate gaze.

"So... You were serious, weren't you?"

I blinked, confused. "What about?"

"That this was going to be your first time."

My cheeks turned bright red, as I looked away. "I... I don't know why someone would lie about that."

"No, it's that... I guess I thought boys your age would be falling over themselves to pass this milestone."

"Well... I mean, I kinda didn't know what I wanted... Aside from kinky shit, I knew that years ago."

She ran a hand along my cheek. "Well I'm flattered to be the one to pop your cherry." Her body leant down to kiss my lips again, sweetly.

"Okay, now that the lovey dovey stuff is out of the way, roll over and stick your ass up." She pulled back with an evil smile, sliding off me and padding over to her luggage. I was swift to assume the position, ass up head down with jeans around my ankles. She returned to slap me on the ass, making me squeak and blush. I turned around to look at her and spied the dangling mass of condomed silicon jutting out from her harnessed panties. Every muscle in my body wanted to jump on it and take her length inside me.

Her fingers, lathered in cool lubricant, pressed softly against my ass and swirled around. The coldness and touch brought squirms and moans in equal measure. She laughed, a devious light shining in her eye.

"You're such a buttslut, Will! I'm so proud of you." Her praise brought more butt wiggling encouragement to my actions. Her hands moved to take hold of the sides of my hips, and I felt the tip of the strapon pressing between my cheeks. The moment was finally here.

"Are you ready?"

I was barely able to contain myself to just a nod. Fortunately, I didn't have to wait long before the tip slowly pushed past my ring and probed my insides. I had played with my fingers before, but this... This was something else entirely. My hands balled at the couch cushions as my back arched to meet the invader. As the whole length settled inside me, I let out a long, lustful moan.

"Are you sure you've never done this before?" Elise chuckled with surprise.

"Well, I had to make sure this was gonna work... You never said I couldn't practice with fingers!"

Her reward for my creative rule bending was a slow thrust of her hips, the pleasurable tingles shooting all throughout my body with the movement. I whined with need, my body thrusting softly against the cock in my rear. Her nails raked down my back as her thrusts picked up, increasing to a steady rhythm that had my mouth open with a constant string of pleasured noises. I thrust my hips in time with hers, slamming together as the tip pressed to its deepest. It was the best moment of my life.

Unfortunately, like most great moments in a person's life, it was over way too soon. My cock was already straining against the cage after a few minutes, and with a few more thrusts I was spurting thick puddles of cum onto my couch cushions. I was so embarrassed, I had expected to last way longer!

Elise smiled and pulled herself out of me, moving beside me to stroke my hair as I rode my orgasm.

"Was it worth the wait?"

I nodded dimly and sheepishly smiled. "I hope I don't have to wait a month for round two."

By her grin, I'd say I wouldn't have to wait even an hour.