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.

Hearing this reminder of our obscene age gap as Mr. Taylor excitedly plundered my anal cavity sent me spiralling into a heaving orgasm that began with vibrations deep in my rectum and spread quickly. I could feel copious pussy juice leaking down my inner thighs and dripping onto the bedspread as my no-longer virgin arsehole squeezed and clenched around Mr. Taylor’s thick shaft.

The intense shuddering inside me must have triggered Mr. Taylor’s climax too because within seconds he had stopped thrusting and forced his cock as far past my stretched sphincter as he could, holding it there with a tight grip on my soft thighs. He gasped and groaned as thick hot cum pulsed out of his turgid member and flowed quickly into my quivering little rectum. As he held me tightly in this position I could feel ropes of his thick gloopy semen continue to burst into my tight arsehole and slip deeper inside me. When Mr. Taylor eventually pulled backwards, the last remnants of his slimy climax spurted onto my pale arse cheeks and dribbled down my crack to join the globs of gooey cum already slipping out of my gaping anus.

He looked down at my arse quickly, and then collapsed sideways on the bed, exhausted by the intense effort it had taken to squeeze his large organ in and out of my tiny sphincter so forcefully. I slumped forward and relaxed, still shivering from the most intense orgasm of my life and revelling in the sensation of my boss’ slimy semen leaking copiously from my most private orifice. I knew then that Mr. Taylor was right: I would definitely be back for more.

For more than a week after Mr Taylor had taken my anal virginity in a hotel room, I did not see or hear from him at all. I had replayed the sordid encounter in my head countless times, and often felt my pussy clench involuntarily when I pictured the scene as it had unfolded. Even after the tenderness in my arse had faded I couldn’t stop thinking about the middle-aged married man squeezing his swollen cock into my rectum until his testicles slapped gently against my slippery labia. I shivered with longing when I remembered how his warm cum seeped out of my stretched sphincter and soaked my underwear as I hurried home afterwards.

So my stomach fluttered when I got an email from Mr Taylor asking me to attend a personal progress review in his office that afternoon. I couldn’t help shifting in my seat when I imagined being alone again with such a confident and dominant man who clearly lusted after my supple nineteen year-old body.

I was silently grateful that I had gone to the effort that morning of putting on skimpy black underwear and sheer black lace-topped stockings with a suspender belt. After lunch I checked my makeup, undid one more button on my blouse, and walked a little too quickly along to Mr Taylor’s office.

When I entered the office I was surprised and immediately disappointed to see that Mr Taylor wasn’t alone. Across his desk sat another of the senior executives at the firm, a chubby, balding man whose suit was slightly too tight. After closing the door, I greeted both men politely and took a seat.

“I have taken the liberty of updating Mr Hitchens on your recent progress,” said Mr Taylor, smirking at me. I looked between him and Mr Hitchens in confusion. “Don’t play dumb now. I’m talking about the services you have been providing me personally,” he continued and I stared at him in disbelief. “Don’t worry, your secret’s safe with us both,” he said and I suddenly became acutely aware of Mr Hitchens leering at me with a crooked smile. “Mr Hitchens is only here because he wants to see your pert little arse in action for himself.”

“Mr Taylor insists he won’t share you with anyone, but I guess I can still enjoy the view,” said Mr Hitchens as he leaned over and laid a sweaty palm on my thigh. I realised the awful predicament I was in. After my boss had penetrated my anus with his large cock and injected me with copious amounts of his sticky semen, he was blackmailing me into spreading my arse cheeks for him in front of another middle-aged man.

Mr Taylor tapped his thigh and I walked over to sit in his lap, almost in a trance. I was still strongly attracted to this virile older man but I had never imagined letting anyone watch him sodomise me, let alone another senior member of staff. It was clear that now I had no choice.

Mr Taylor slowly unbuttoned my blouse and pulled it off my shoulders before yanking off my bra. He turned his office chair until I was facing Mr Hitchens across the desk and started to gently squeeze my tits. They’re quite small, but my perky pink nipples point upwards nicely and they quickly stiffened as Mr Taylor showed me to his colleague. I blushed furiously and stared at the ground as Mr Taylor jiggled my teenage flesh and Mr Hitchens stared in awe.

“Isn’t she tasty? My cock’s hard already. She really loves it up her arse, you know.” Mr Taylor nodded slowly as Mr Hitchens unzipped his tight trousers and drew out an average-sized flaccid penis. As he gently coaxed it to life, Mr Taylor stood me up and removed my skirt, then spun me around in a circle to show off my young body in the tight, slutty black underwear. I was terrified he would discover that my tiny lace thong was wet with arousal. When Mr Taylor unzipped his trousers and untucked his shirt, I was anxious that he was going to invade my anus straight away. However, he sat back down in his chair and forced me to my knees.

“Bring your chair round for a better view,” he told his colleague as he pushed my head down into his lap and I automatically accepted his engorged sexual organ into my mouth. It was almost completely erect already and I started to bob up and down slowly, running my tongue over every inch of his shaft and occasionally drooling extra saliva onto it.

I glanced up into Mr Taylor’s face and then without thinking I looked over at Mr Hitchens. His cock was extremely hard now and he was holding it tightly while he watched me fellate another old man. I maintained eye contact with Mr Hitchens while I rubbed my boss’ spitty cock over my chin and my cheeks, coating my face in saliva and shiny precum. Mr Taylor laughed gently then forced my head back down until the hot bulbous head of his member was pressed against the back of my throat.

“You’re not meant to be enjoying this. You’re mine and you’re here for my pleasure. Make sure you get my cock nice and slippery with your mouth because you where it needs to go next.” As I focused on giving my middle-aged boss the best blowjob I could muster, he asked Mr Hitchens how often he got to come in someone’s mouth these days. “My wife hasn’t blown me in ten years. I don’t care now that I have a teenager to do it.”

Mr Taylor shifted in his chair slightly and I wondered if he was going to spurt his come into my mouth while Mr Hitchens silently watched on. Despite the circumstances, I was extremely turned on and I worked faster in the hope of swallowing some of my boss’ slimy semen. I reached up to tickle his testicles but he pushed me away and told me to keep my arms behind my back while I serviced him. After a few more moments Mr Taylor sighed and leaned backwards in his chair, starting to pump his hips upwards to force his shaft deeper and deeper into my warm mouth. As he grunted softly I felt deliciously warm cum coat the back of my throat and my tongue. My boss moaned and held my head down tightly as his big shaft continued to expel gloopy semen into my mouth.

“I’ve been saving that hefty load for you, you know. It was meant for your arse but your soft lips are good too,” Mr Taylor said as he released my head and looked down at me. I hadn’t yet managed to swallow all of the ejaculate and he lifted my chin and turned my head to show Mr Hitchens the pale creamy dribbles at the side of my mouth. Mr Hitchens was sweating profusely now as he masturbated furiously.

“You said I’d see it in her arse. Do it soon, before I cum,” he said to my boss desperately. Almost instantly I was dragged to my feet and forced forwards across the desk. My soft pliable buttocks were framed by my black suspenders and split in two by the string of my black thong. Mr Taylor shoved one knee between my legs to splay them apart, then spat on his hand and massaged the saliva into my tiny anus.

I was dripping with arousal at the thought of this older man violating my arsehole again and I pressed my bare tits into the wooden desk in order to lift my arse higher, towards Mr Taylor’s rapidly hardening organ.

“Spread your arse apart and show us your little hole.” After a couple of sharp slaps which reddened my peachy teenage arse cheeks, Mr Taylor pulled my thong out the way then leaned forward and pushed his swollen cockhead into my anus. With increased pressure, it popped past my sphincter and the discomfort faded away as my boss quickly sank his thick shaft further into my rectum. Being taken forcibly by such a well-hung man had obviously stretched my anus permanently because this time Mr Taylor was able to start thrusting straight away.

With his trousers round his ankles, Mr Hitchens shuffled round to get a closer view of my little pink hole stretching around a large erect penis.

Dizzy with arousal, I began to deliberately ripple my rectal muscles, massaging my boss’ engorged organ as it slipped in and out of my anal cavity at an increasing pace. I was still prying my arse cheeks apart to facilitate easy viewing of my invaded anus, so my face was pressed harder into the desk with every thrust from behind. In minutes I felt the familiar creeping of an anal orgasm in my lower belly and I whimpered then moaned as it engulfed my senses and made my whole body tremble. My knees buckled but the force of Mr Taylor’s continuous penetration held my body over the desk as he neared his climax.

With a final violent thrust, my middle-aged boss ejaculated into my rectal passage and quickly filled me up with frothy jism. I squirmed beneath him as more and more semen flowed into my arse and marked me as Mr Taylor’s private property. I felt the delicious warmth seeping upward and deeper into my bowels than ever before and I over my shoulder I directed my most subservient and grateful gaze at his handsome face. He looked over at Mr Hitchens as he withdrew his softening cock from my anal cavity and staggered backwards.

Mr Hitchens stepped forwards and within moments had squirted his creamy cum over my lower back and the tops of my quivering arse cheeks. My fingers were digging into my flesh now but I continued to expose my whole bum crack and puckered arsehole as he directed a second spurt of cum onto my anus itself and my upper thighs. My garter belt and thong were completely covered in this fat old man’s white froth. It trickled all over me as Mr Taylor’s cream slowly emerged from my contracting anus and coated my bald pussy lips. My lower back, bum and thighs were shiny with their gooey mixed ejaculate and I could still taste Mr Taylor’s semen in my back of my throat.

Both men had pulled up their trousers and stood back watching as I quickly pulled on my bra and stretched my soaked thong back into place between my sticky arse cheeks. I looked around desperately but there was nothing to wipe myself with. I buttoned up my blouse then stepped into my skirt and pulled it up over my slimy bum. The skirt stuck to me as I tried to straighten it over my stretched underwear and the copious volume of gloopy semen that still dripped over my backside. The two middle-aged executives chuckled quietly as I walked smartly out the door and returned to my desk.