First Time Anal With My Boss

After I had finished school, I began training as a paralegal, which, aside from going to law school, required practical work at a lawyer’s office. The law firm I worked with was a mid-sized company with just a handful of lawyers, all of which pretty much ran their own office. The attorney I was assigned to was a young woman who had only finished her studies a few years ago herself. She was specialized in family law and was also a criminal defender.

Her name was Anja, and she was all sorts of beautiful. She was tall and slender, looked sporty and well-trained. She had natural blonde hair which she kept straight and simple at about chin-length, framing her pretty and delicate face that didn’t have or need much make-up to shine. For the most part, when she didn’t have any appointments at the court, she dressed in comfortable, loose clothes that completed her easy-going, straightforward look.

For the most part I did office work for her, keeping her files in shape and writing a few letters for cases she was working on. It wasn’t very hard work and the office days were short, so I enjoyed my time there immensely. The only times I was not around her were when it came to lunch, as she used to stay in her office by herself for that, while I went out to the city to grab a bite to eat. She was eating very healthy too, always just bringing salads, vegetables and an occasional yoghurt to work, so I assumed she must be vegetarian.

I learned better one day when I returned early from lunch, as it had started raining. The office was empty and I had just hung my coat and stored away my handbag when I heard a faint, shrill shriek. It came from her office, whose door stood slightly open. Fearing that something was wrong, I quietly snuck up to the door and peeked inside.

She sat reclined in her chair, which was tilted as far back as possible, with both her legs resting on top of the desk, spread slightly apart. The white pants she had worn earlier were gone and her legs were bare, while the tight blue t-shirt she was wearing was pushed up slightly. Both of her hands were down between her legs, hidden by the desk, while her head was tilted backwards and her eyes closed.

Discretely, I entered and closed the door behind me. She only noticed me when the lock snapped, staring at me wide-eyed and speechless. I put a finger to my lips, indicating that I’ll keep quiet if she would be too, and slowly walked towards her. Aside from the one time with my teacher and a few girlfriends at school I didn’t have many experiences with women, but I was at a point in my life when I felt confident and curious enough to finally explore love and sex on my own, and that gave me the courage to walk up to her and gently caress her naked leg, running my hand along the inside, slowly up towards her thigh.

She followed my movements, still staring wide-eyed, but slightly more relaxed when I began caressing her. When I got closer, I could smell her faint cologne and caught a glimpse of what was going on behind the desk. She was wearing a white thong that she had shifted to one side, which revealed a pair of very long, very large labia below a thin strip of medium blonde pubic hair. And sticking out between them was the short end of a long, green cucumber that she had kept in the fridge all morning, slick and wet from her juices.

My fingers moved up along her thighs as I leaned in, my other hand resting gently on her small, but firm, breasts, rubbing and pressing against them through her shirt. I grabbed the cucumber and began to turn it, twisting it inside of her as I moved it slowly in and out. She closed her eyes again and began moaning softly once more. “Th… the door,” she whispered, trembling as I started moving the green shaft faster and harder inside of her.

“Mmmh, you don’t want anyone else to walk in on you, huh?” I asked cheekily, grinning at her without stopping the treatment of her pussy. She shook her head, almost too wild. Slowly I backed away. “Well, we better lock it then,” I said, helping her up, deliberately leaving the cucumber lodged deep inside her. She walked, uneasy with her thighs clenched together over to the door and inserted her key, locking it hastily. I came up behind her, suddenly slapping her bare butt hard as I grabbed the cucumber once more, pushing it hard up her big wet twat.

She groaned, leaning against the door, pressing her cheek on it as I began fucking her cunt strong and hard from behind, hitting the back of her pussy with the cucumber every time I thrust it in. It was painful, and yet it was just the kind of fuck she needed, panting and groaning as I held her pinned against the door, keeping her in place with my body pressing heavily against hers. I held the cucumber now in both hands and just rammed it inside her, as hard and deep as I could, the thought of fucking my boss violently while she could do nothing to defend herself spurring me on even more.

Soon, she came, drooling a little out of the side of her mouth as her body shook and shivered, her legs giving in underneath her. I quickly caught her arms, holding her steady as she reached to her desk for support, giggling uncontrollably and still shaking all over her body. In the end, she leaned across her desk, catching her breath while moaning “Mmmmmmhhhh” with her eyes closed.

I smiled happily, glad that I could make her feel this good. “God, that was great,” she said. “I didn’t know you were…” She paused, looking into my eyes.

“That I’m a lesbian?” I said, grinning back at her. “Or that I’m such a good fuck?”

She giggled again. “Well,” she replied, “I certainly think you deserve something in return.”

“God, I hope so,” I said laughing, rounding her desk and pulling myself up on it. I was still wearing my brown leather boots and a long, green knit-dress with buttons all the way down its front. I began opening them from the bottom up, revealing more and more of my legs until the fact that I wasn’t wearing any panties could no longer be hidden.

“Mmmh, you’re always ready, huh?” she said as she walked over in front of me, looking down at my chubby pussy and auburn pubes.

“Always…” I replied, leaning back onto the files and law books that littered her desk, spreading my legs towards her. She slowly pulled the cucumber out of herself and began running its slimy surface along my wet labia, mingling her juices with mine while her other hand ran through my pubic hair with her thumb pressing hard on my clit.

I trembled in anticipation, wanting to get something inside of me and be fucked just as hard and deep as I had fucked her earlier. “So then, how do you like it?” she asked, looking down at me a little insecurely.

I reached down and pulled up my legs, pulling my cunt wide with both hands. “Just fuck me,” I whispered, aching for her to stuff me with that cucumber.

She slowly pushed it into my muff, being almost too gentle as she didn’t know how hard or deep she could go. I leaned back patiently, feeling the vegetable spread my insides, inch by inch, widening my cunt further than anything else I had inside before. It was good-sized, but it felt massive, much bigger than it looked, giving me an incredible feeling of fullness.

She moved it rhythmically in and out, getting deeper and deeper as more of the shaft got lubricated by my copious cunt slime. In between thrusts she would occasionally pull it all the way out and lick it, obviously enjoying the taste of our twat juice salad. It was not until she had bitten small bits of it around the top, making it a little thinner and more pointy, that she suddenly moved the focus from my pussy down to the area between my buttocks.

Without a warning, she pressed the wet, thin, slick end of the cucumber on my anus. Having never done anything anally before, my first impulse was to try to stop her. It felt painful, and wrong, and somehow unpleasantly like I had to poop. But then it came over me. This was the naughtiest thing anyone had ever done to me so far, trying to fuck me into my asshole with a cunt-slime covered cucumber, uninvited. It made me feel raunchy, and horny, and all kinds of dirty, and so I relaxed and laid back, letting her pass.

At first, the sensation was like my asshole was ripped open. The vegetable might have already felt massive in my cunt, but it felt gigantic inside my tight, virgin ass. She went about it slowly, only pushing it millimeters at a time, until my sphincter had adjusted to the girth of the shaft and the passage got easier. Then she began to fuck me raw.

The vegetable thrusted hard up into my intestine, making me feel incredibly full. At the same time, the pressure and friction gave me an unimaginable feeling of fucking, dirty and depraved, the thought of being an ass-whore making me additionally wet. And then it happened: With every thrust, my pussy began to squirt, small fountains of liquid, erupting out of my empty hole and gushing all over my furry pelvis and dripping down on the cucumber in my ass, wetting it even more.

Anja eyed it curiously at first, but then bent down and began to slurp on my muff, sucking and swallowing whatever came out of it while she penetrated my ass with the thick, hard cucumber until it was raw.

I had come countless times before she stopped, leaving me exhausted, sweaty and soaked in my own juices on her desktop. I laid there, relishing the feeling for a long while, feeling the waves of orgasm slowly ebb and subside. When I had finally caught my breath, she had dressed and was munching on the cucumber, grinning at me from her chair.

After that, we frequently spent our lunch together in her office, though I never told her that she was the first one to fuck me up the ass.

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