Since starting my first professional job a few weeks ago, I had quickly begun an intimate relationship with an associate director at the firm, a tall, broad-shouldered and grey haired man who was at least thirty years my senior. At nineteen years old and very naïve, I hadn’t considered the implications for my career the first time Mr. Taylor had called me into his office and pushed his hand up my pencil skirt to squeeze the soft flesh of my bum between the top of my stocking and my lacy thong. Despite the fact that he was married, we had had several more hurried encounters where he had fondled me under my clothes or had me straddle him and bounce gently up and down while he massaged my soft, pliable arse cheeks until he came in his pants.
These encounters culminated in a lunchtime session where Mr. Taylor held me face down over his desk and wanked himself until he squirted his warm cream over my trembling thighs and arse, keeping me pinned there while it slowly dripped down between my legs, over my little virgin anus and my smoothly waxed pussy lips. I had become infatuated with Mr. Taylor during our series of intense wordless liaisons, so when he told me to meet him at a smart hotel in the city centre the following evening I was apprehensive but very excited.
I prepared carefully for my meeting with Mr. Taylor, despite the fact that he hadn’t given any real indication of what we were going to do. My whole pubic area was completely waxed smooth, and I moisturised my firm arse and thighs before I pulled on a tight little black thong which cut into my hips and clung tightly to every fold of my soft labia. I deliberated about wearing a bra because my small tits are naturally perky, but I eventually decided on a black transparent lace bra that contrasted nicely with my creamy teenage flesh. I slipped on a simple black dress and high stiletto sandals that forced my bum up and outwards as I teetered into the hotel reception. Mr. Taylor was waiting for me and took me firmly by the elbow, steering me upstairs and into a large bedroom suite.
“I think you know why you’re here,” he growled at me after the door had slammed behind us, still gripping my arm tightly. I stared at him, speechless, as his tall muscular physique and complete self-confidence made me weak at the knees. “You’ve been flaunting that tight little arse right in front of me for weeks. I haven’t been able to think about anything else. My wife doesn’t let me near her arsehole but luckily since you’re my lowly employee, you don’t have any choice in the matter.”
I shivered with apprehension and excitement as Mr. Taylor pulled my dress off over my head and forced me onto all fours on the bed. I felt my sex clench as his hands ran over my thighs and he pulled my sticky thong upwards, digging even deeper into my juicy cleft and gently sawing back and forth over my small crinkly anus. He paused for a moment to tear off my bra and I turned my head to see him frantically pulling off his clothes.
I felt the bed shift as he knelt behind me and pressed his naked flesh against the back of my legs. He finally tore off the tiny thong completely and rubbed a large thumb over my anus, dipping it into my slimy pussy to collect lubrication for my virgin hole. He repeated this several times, until the whole area between my swollen clit and my little pink anus was completely slicked in my sexual juices. I gasped and mewled as he began pressing his finger into my anal passage.
“You’re going to enjoy this, you know. And even if you don’t, you’ll still be back for more if you want to keep your job.”
I looked sideways and in a set of mirrored closet doors I saw the whole scene as it unfolded: my firm little teenage body, perched on all fours with my juicy tits dangling down in front of me and my legs spread wide apart to allow my boss complete access to my genitalia. It was only then that I got a proper look at Mr. Taylor’s cock, which was long, thick and very veiny as he slowly massaged my vaginal juices over his shaft and its bulbous head. He was staring down at his cock and my arsehole and carefully lining up his organ with my last virgin passage.
I pressed my face into the bedspread as I felt the tip of his member nudge against my anus. I was pressed face down as a married man in his fifties slowly but surely penetrated my anal cavity. The extent of my arousal was masking any initial discomfort and I squirmed and moaned in pleasure as Mr. Taylor’s shaft inched its way further into my arsehole. I already felt completely stuffed full with his pulsing organ but it took several minutes for his greying pubic hair to touch my stretched arse cheeks. I knew then that he had claimed my body entirely for his own and I would always be under the control of this powerful older man. He could go home and screw his wife whenever he liked but since his delicious conquest of my virgin anus, my body belonged to Mr. Taylor alone.
Mr. Taylor pulled my taught bum cheeks further apart and stared down as his shiny shaft edged in and out of my obscenely stretched anus. My rectum pulsed and rippled around his engorged shaft as Mr. Taylor’s giant erection massaged my most intimate areas. One of his hands was pressing into my lower back to hold me still as he penetrated me, but with the other he grabbed my hair and yanked backwards. This caused me to arch my back, opening and extending my anal canal even further to allow the maximum depth of penile insertion.
Mr. Taylor had been quiet compared to my high-pitched grunting as he stirred intense pleasure in my lower belly, but he began to breathe more heavily as his thrusting increased rapidly in pace and vigour.
“I can’t believe my cock is jammed deep in a teenage anus,” he hissed as he continued to pull his erect penis completely out of my wrinkled arsehole before squashing it quickly back in down to its thick root.
“I’ve never been inside such a hot tight arse,” he continued, pronouncing each word in time with a violent thrust.