Young woman enters unusual arrangement with powerful boss.

After graduating, I took a job as a secretary to a very successful businessman in a large office. I considered myself over-qualified for the job but at twenty years old I wanted a steady income without too much responsibility, and I had heard from a friend that the position was available. The novelty of professional life had not worn off yet, and I still enjoyed dressing the part for my job, which was mainly administrative tasks and welcoming my boss’ clients into the office. I usually wore a silk blouse and tight pencil skirt with stiletto heels, which accentuated my tall and very slim figure, and more than once I noticed male visitors’ eyes eagerly raking over my pretty face and slender frame.

One morning my boss called me into his office and dictated a few letters for me to type up. Mr Charles was in his mid-fifties, with grey hair and a tall, toned physique. He wore immaculate business suits and even a shy twenty year old noticed how handsome and attrActive he was. As I turned to leave his office, Mr Charles called me back, and said how pleased he was with my performance so far. He said his clients were always very complimentary of his young secretary, and he wanted me to make sure I kept up the good work. Something about the way Mr Charles’ eyes lingered on me as he complimented me gave me a shudder of excitement as I walked back to my desk.

That night, in bed with my boyfriend from college, my mind kept straying back to Mr Charles and his deep, commanding voice. As my boyfriend squeezed and fondled my small tits, I closed my eyes and imagined it was Mr Charles’ strong, lined hands instead. I let my mind wander to what it would be like if it was my middle-aged boss who was kissing my neck and sucking my soft pink nipples, and I inadvertently gasped and arched my back with pleasure. My boyfriend was nice enough but far from spectacular in bed and he had never provoked this intensity of response in me before. Encouraged, he climbed on top of me and tried to stick his average-sized cock into me. I stopped him and grabbed a condom off the dresser, handed it to him and lay back down, looking away.

“Baby, you know I hate condoms. I want to feel your little pussy properly. I promise I’ll pull out, baby. And I don’t see why you can’t go on the pill anyway.”

I sighed and refused, like I always did, because I didn’t see why I should interfere with my hormonal balance just for him to get off, and anyway, I preferred to have his semen neatly deposited inside a condom than on me or the bed sheets. After he put on the condom, I lay there facing away as he slid in and out of my pussy at a regular pace, and imagined what Mr Charles’ cock would feel like squeezing into me. After a few minutes of boring intercourse, my boyfriend grunted and spasmed, squirting his meagre ejaculate into the condom, and then he rolled over and fell asleep. I lay awake for much longer, slipping my small hand downwards and rolling my clit between my fingers while picturing Mr Charles cradling me in his arms as he massaged me to orgasm.

In the morning I still felt frustrated at last night’s unsatisfying sex, and extremely horny as a result. I pulled a tight black thong up my long legs and fitted it snugly against my anus. I let the gusset nestle between my smooth bald labia so it was basically hidden, and pulled sheer black stockings on, clipping them onto a lacy suspender belt. My boyfriend came out the shower and gawped at me, then tried to fondle my bare tits and grope my ass, but I pushed him away and told him I would be late for work. His small dick was semi-erect under his towel but it seemed pathetic to me and I turned away. Usually I wore a slightly padded bra under my work blouses to disguise my two silver nipple piercings, but in my frustrated mood I chose a very sheer black lace bra, through which the nipple jewellery clearly showed.

At my desk I could not stop thinking about Mr Charles and found myself making excuses to go into his office just to be near his magnetic presence. I kept picturing Mr Charles grasping my young flesh, and wondering what his cock would look and feel like. Through the open office door, I watched Mr Charles lean back in his chair as he spoke on the phone, and saw the outline of his strong shoulders press through his shirt. I stared at his neck as he talked and imagined kissing his sharp jawline and ingratiating myself to his powerful presence. I was acutely aware of my lace thong stretched taut over my anus and deep inside my labial cleft, and I squirmed desperately in my seat before turning back to my computer. Within a short period of time I had become completely infatuated with my boss and my naturally timid nature was nearly overridden by my sexual fantasy.

By lunchtime, I was completely overcome. Under my tight black skirt, I could feel the soft skin of my inner thighs was slippery with arousal, and my heart was skipping with nervous excitement and desire. I walked in a daze to the small restroom on our floor of the office and inside I leaned against the wall with one arm outstretched, my back to the door. I hitched my skirt up over my hips, spread my legs wide and finally allowed myself to probe my juicy, swollen pussy. I stretched the thong aside and pushed three fingers deep into my vagina, gasping and arching my back with temporary relief. My clitoris felt enormously swollen and so tender I could barely touch it. I settled into a frantic finger fuck, picturing Mr Charles behind me shoving a large penis fiercely into my small hole, and was on the brink of an orgasm within a minute. But before I could cum, the door behind me swung open.

In hindsight, I wonder if subconsciously I meant to leave the door unlocked in the vague hope that he would discover me in there, bent over against the wall with my hand nearly stuffed inside my dripping sexual hole. I stopped moving as Mr Charles took in the sordid sight, including my tight lace-topped stockings and suspenders, and the slight sheen of sweat on my flushed cheeks as I turned to face him.

“Finish yourself off then meet me in my office straight away,” he said in a measured voice. I caught a glimpse of his pants tightened over his bulging crotch, and nodded. Tears of humiliation prickled in my eyes and my heart thudded with fear and shock, but not enough to prevent a shattering orgasm almost immediately after Mr Charles closed the door again. I fell to the floor on my hands and knees, gasping for air as my whole body clenched and squeezed with pleasure. Sweat gathered at my hairline and I could feel my blouse sticking to the small of my back, but I composed myself as best I could and slowly walked next door to face the consequences of my sluttish behaviour.

Mr Charles was sitting behind his desk and started speaking as soon as I sat down opposite him. “This is the arrangement I propose, and you will accept it in its entirety or we will not speak of it ever again. I will have unfettered access to your body at all times, which will extend to its use by me or other men authorised by me for sexual purposes, but also to where you go, what you wear and what you eat. No one else will have access to your body and while you need not end your relationship with that college boy, you will not allow him any access to your body or afford him any sexual gratification. I will continue to have an intimate relationship with my wife and you will make no complaint.

“However degrading or unpleasant you judge my demands for sexual gratification, you will meet them willingly and subserviently, and in return I will protect you from lasting harm. My access to your body includes but is not limited to penetration by my penis, tongue, hands, or any other body part or object, of your three bodily orifices: your mouth, your vagina and your anus. I will ejaculate wherever I please, including but not limited to your mouth, throat, face, hair, neck, breasts, vagina, labia, buttocks, anus, and rectum. You will welcome my ejaculate on and into your body without complaint and never mention nor expect the use of barrier contraception methods. You will visit my doctor and embark on a course of oral contraception as prescribed by him. Do you require any further details?”

I shook my head slowly, feeling my pussy on fire with excitement and lust. After mediocre relationships with boys my age I had never imagined the depth of sexual longing I could feel for a man, and nor had I ever imagined feeling so eager to please and willing to sacrifice my independence and dignity for a man’s selfish sexual fulfilment.

“If you accept this arrangement, we will not formalise it in writing but start as we mean to go on. Since contraception is not yet in place, the contract will be sealed by an eager and sincere act of fellatio and an initial acceptance of my semen into your body.”

Mr Charles pushed his chair away from the desk and patted his thigh.

“Come here and seal the deal,” he said in a quiet, gentle voice. I approached without hesitation and almost fell to my knees in front of him. He unzipped his pants and shuffled in his seat to pull out his erect penis. My first sight of his organ caused shivers of apprehension and lust down my spine. I stared numbly at the nine-inch shaft, as thick as my wrist and swollen purple with thick veins running its length. Precum oozed from the shiny bulbous head and ran in a glistening rivulet down the side of the fascinating organ. Mr Charles softly stroked my hair and tilted my chin upwards with one finger.

“My sweet girl. I won’t force you into anything. But I suspect I wouldn’t need to anyway. Start slowly if you feel afraid. Just lick away my semen as it emerges. I will take care of you.” I nodded and ran my tongue over my dry lips. Leaning forward, Mr Charles’ hands still resting lightly in my hair, I extended my moist tongue and ran it up the side of his slimy cock. The heat and musk of Mr Charles’ arousal was addictive to me and I shuffled forward on my knees quickly to take the top of the penis into my warm mouth. My lips were stretched tightly around the huge swollen shaft and I waggled my tongue gently against the hole where large blobs of precum continued to emerge. I was completely absorbed, and I readjusted my kneeling position again to gain better access.

“There’s no rush, my girl,” chuckled Mr Charles, but he also leaned backwards and pressed his groin upwards, now filling my whole mouth with his stiff sex. He sighed and closed his eyes. “You’re perfect, you know. So beautiful and fresh and innocent. My wife refuses to service me with her mouth and throat but you know better, don’t you my sweet girl.” My lips made quiet slurps and sucking noises as I continued to fellate my boss enthusiastically. Part of my mind was distracted by the mention of Mrs Charles but I forced the thoughts away by forcing more thick penis into the opening of my throat. There was still about four inches of Mr Charles’ erection exposed, but I pushed down harder until it slowly but surely slid into my tight hot throat.

“Jesus Christ, my girl. I thought I was going to have to train you to do this. You’re beautiful and talented too.” And he grunted and suddenly grasped my head more tightly. Until now Mr Charles’ big hands had just been resting in my hair as I bent my neck, but now they asserted their own rhythm on my movements and sped up the pace at which the enormous erection thrust in and out of my throat. I did not gag but my eyes watered as I lost my breath, and as my jaw was stretched even further, a mixture of drool and precum accumulated on my slippery lips and dribbled down my chin. Mr Charles had built up a lot of speed now, but suddenly stopped moving his hips and directing my head, and forced my face downwards almost until my nose touched his groin. He grunted and I felt his penis twitch as he climaxed in my throat. Warm jets of ejaculate sprayed into my contracting throat and coated my tonsils in delicious sticky goo. Gradually, Mr Charles moved my head upwards again so that the remaining pulses of salty semen streamed into my mouth, coating my soft tongue and gathering in my cheeks before I gulped it down. Despite my previous preference, it didn’t even cross my mind to avoid drinking Mr Charles’ precious semen, and there was a considerable volume collected in my stomach before he leaned back and my lips were pulled off the head of his cock with a slimy pop. I licked my lips, panting and out of breath, and looked up at Mr Charles, desperate for some sign of his approval. I was consumed by a desire to meet his needs and gratify his urges by any means.

“Well done, sweet girl. You did very well and I am pleased we have sealed our arrangement. Go home now and I will make an appointment for you to visit my personal doctor in the morning.” He stroked my face once more, then arranged his pants and turned back to his desk, obviously dismissing me. I staggered out of the office, wiping the rest of my boss’ cum off my flushed face.

I sat nervously in the doctor’s examination room the next day and answered in a quiet voice as he took details of my name, age and address. The middle-aged male doctor, who had raised his eyebrows when I told him I was just twenty, seemed brusque and rushed, and I had not protested when he told me a medical student would be observing the consultation. The student was a muscular, confident young man of about my age, and he took a seat at the edge of the room with his knees spread and his arms folded across his wide chest.

“Mr Charles has explained your arrangement to me but I must hear the details directly from the patient for my records, and of course for the sake of the student’s education. I need full and frank answers from you and you must not omit any details. I will be making a permanent note of your answers to remain on your medical file. Mr Charles, who will be paying your bill, obviously has unhindered access to the contents of this file as well.” I nodded meekly and then cast my eyes back to the floor.

“For how long have you been sexually active?”

“Since I was 16.”

“Okay, so four years. And what is the age range of your former and current partners?

I paused. “Mid-teens to… mid-fifties, I guess.”

“Okay, so ranging from about your age to more than thirty years your senior. I see. And how many sexual partners have you had?”

“Four.”

“Now I have some specific questions about your experience of male ejaculation. Has a man ever ejaculated directly into your mouth, vagina or anus?”

“Into my mouth, but only once. I have always insisted on a condom for sex. And I’ve never even had anal sex, the thought of it freaks me out.” I blushed as I remembered Mr Charles gently holding my head down as he ejaculated into my slippery mouth the day before.

“Would you say you had an aversion to fresh ejaculate?”

I paused. “Maybe… I suppose I just never felt connected enough to someone to want to share that with them.”

“So would it be fair to say you have found sexual intercourse relatively unfulfilling in your lifetime? How often do you reach sexual climax?”

“I suppose so,” I said, blushing even harder now. “I only ever cum when I touch myself, never just from sex with someone.”

“Have you ever been filmed or photographed while nude or engaging in a sex act?”

“No…” I wondered where the doctor was going with this line of questioning but he did not give me much time to think about it.

“And have you ever engaged in sexual intercourse which involved stimulation or penetration of your anus by any body part or object?”

“No!”

“I see. I expect Mr Charles will be pleased that you are almost entirely uncontaminated by other men. Being a virgin would be quite something, but I don’t blame you for failing to keep men away. You really are quite something to look at.

“Look,” he said, gesturing to the medical student to come over from his observation point to where we were sitting. “The soft, full lips imitate hairless labia swollen with arousal. The flush in her cheeks gives a very youthful and innocent glow and her shallow breathing is suggestive of orgasmic gasps. These are the signs to look for when assessing a young woman regarding contraception and sexual health. She is clearly a very sexual being and I’m sure you can empathise with the men who have previously sought to use her body for their own gratification.”

The medical student nodded slowly and walked around me, eyeing up my slender figure, which was now almost shaking with nerves and anticipation.

The doctor then addressed me again, continuing his previous line of questioning. “Have you ever had sexual intercourse with more than one partner simultaneously? Examples would be accepting vaginal and anal sex at the same time, or receiving a penis in your mouth while engaging in vaginal and/or anal sex.”

“No!” I said, quite shocked by the question. The student smirked and slid back into his seat.

“Mr Charles has a right to know these things. And he will be glad to hear there are some things he can still introduce you to. Regarding oral sex, how often do you find your gag reflex interferes with your pleasuring a male partner?”

I stared at him and my cheeks burned. Maybe Mr Charles had told the doctor about my hungry cock-swallowing the day before. “I don’t really have a gag reflex actually.”

“And so you accept erect penises deep into your throat? Willingly?” The doctor raised his eyebrows at the thought but I also saw him shift in his seat and rearrange his pants.

“Yes. How many more questions are there?” I was beginning to feel extremely humiliated as the doctor probed my filthy sluttish tendencies in front of his colleague, and felt increasingly uncomfortable that he was finding my responses arousing.

The doctor chuckled and typed my response into the computer. “Don’t worry, that’s all the questions for now. Mr Charles will undoubtedly be taking care of a few of these matters quite soon. I will prescribe an oral contraceptive which will be effective immediately. I note that you have no sexually transmitted infections so I will instruct you not to use condoms any more. You owe Mr Charles the pleasure of your bare flesh, and you ought to allow him to coat you in semen. It’s very good for the complexion, you know!”

I was aghast at the tone of the doctor but glad he would give me the pill I needed to meet Mr Charles’ demands. I took the printed prescription, blushing, and turned to leave the office but the doctor called me back.

“Not so fast. There’s still the physical exam to take place. Please lie on the table and spread your legs. There will be no need to remove your clothes yet.”

I shuddered with dread but was desperate to follow Mr Charles’ instructions so I cautiously mounted the table and lay back with my legs open. The student pulled my skirt up over my hips and unclipped my stockings from my suspender belt. He gently ran his fingers under the waistband of my tiny thong, then very slowly rolled it down to my mid-thigh. Looking at the doctor for further instructions, he then gently pulled apart my labia to expose my clitoris. For some reason the student was not wearing latex gloves and I knew he could feel my arousal as he probed deeper towards my pussy. He pressed one finger into my vagina and I inadvertently gasped then cleared my throat.

“Okay, we mustn’t stretch out the young vaginal canal before Mr Charles has put it to his own use. I’m satisfied with what I’ve seen already, so if you could just turn the patient onto her hands and knees,” said the doctor to the student.

The student helped me turn onto my hands and knees on the examination table, my thong still rolled down and skirt pushed up towards my waist. I saw that now the student also had a large and unconcealed erection pressing through the front of his pants. My sheer black stockings had slithered down my smooth thighs and wrinkled at my knees. The doctor let out a quiet whistle.

“A very nice example here of an unviolated anus. Do you see how the sphincter remains tight and extremely small? The surrounding skin is soft and smooth and the fleshy buttocks will spread to facilitate penetration of the anus. The doctor pressed a gloved finger against my anus and pushed firmly but it did not yield. “Yes,” he said, almost to himself, “Mr Charles will be very pleased. Lets get the photographs and then we’re finished for the day.”

By this point I was so conflicted between humiliation and extreme arousal at the thought of my nubile body being prepared for Mr Charles’ use that I barely registered what was happening. The medical student stretched my ass cheeks apart while the doctor snapped multiple photographs of my anus up close, and also wider shots of me on my knees with my clothes pushed aside. Then the student pulled my labia apart for more close-up photos, and pulled my flesh apart to display the tight pink opening to my vaginal canal. Finally he penetrated me with two fingers and gently teased out some of my sexual juices for a few wider shots of my shiny genitals. The intimate photographs popped up in rows on the screen of the doctor’s computer, showing my flesh from every angle in lurid detail. The photos were uploaded onto my medical file then I was free to go.

I marvelled at the luxury of the glamorous city-centre hotel where Mr Charles had told me to meet him the next evening. I shivered with nerves in the elevator and adjusted the short black dress I had worn with bare legs and high heels. In the elevator mirror I looked more like a scared teenager than the sexy grown-up lover I wanted Mr Charles to see in me. My heart was thumping when I left the elevator and knocked on his hotel room door.

“Good evening, my sweet girl. How are you? You look very beautiful.” Mr Charles looked relaxed with his shirt sleeves rolled up, and he quickly drew me in for a soft warm kiss. With one strong hand in the small of my back and the other on my neck, he pulled me up into him so even in my high heels I was balancing on tip-toes. Still locked together in the doorway, I felt his hand clench at my back and gather up my dress so my whole peachy ass was exposed, my narrow black thong framing it rather than covering anything. The elevator had opened behind us again and the group of business men who came out could see everything. My middle-aged boss was passionately kissing me, while exposing my buttocks and underwear, and I was like putty in his hands as he caressed my ass cheeks and worked my thong down over my hips with one hand, while those strangers watched, until it dropped to the floor at my feet. He groped and pulled at my pliable cheeks and chuckled into my mouth as the onlookers stood there, fascinated.

With a laugh, Mr Charles finally spun round and pulled me into the room, shutting the door on the open-mouthed businessmen. The comfortable hotel suite was dominated by a large four-poster bed, but there was also a beautiful bay window looking out over the rooftops of the city.

“I’m glad you got my message. My doctor said you were very compliant, well done. He sent over some photos of you as well.” My face burned when I realised that Mr Charles had already seen my most private areas, spread open for the camera. At the same time, I knew it was part of our agreement that my body would always be available for him, whether in pictures or real life.

“I… I wanted to obey your instructions.” I hesitated, feeling unbearably self-conscious but also desperate to get closer to Mr Charles again. “I couldn’t wait to see you again.”

“I know, my sweet girl, and I feel the same, of course.” With this, Mr Charles came closer, and, reaching behind me, unzipped my dress so that it pooled at my feet. I hadn’t worn a bra to avoid visible straps, so now I was completely nude, and Mr Charles warm hands pawed at my tits and squeezed my young flesh. He kissed me again, and quickly stripped off his shirt, unzipped his pants, and kicked off his shoes.

“I’m going to use your body now, sweet girl. I care about you and I’ll make sure you feel good, but remember our agreement. You must do your best to please me in every way, okay?” I could feel Mr Charles’ huge penis pressing into my flat belly, and I nodded, my slightly fearful expression betrayed by my stiff pierced nipples and hot, slippery inner thighs. Mr Charles lifted me and laid me down in the middle of the big bed, then settled himself above me and started to press his enormous erection between my legs. Instinctively I spread my legs wider and turned my head sideways as I felt the uncomfortable stretching sensation spread. Mr Charles took my head in both hands and straightened it so I was looking up at him.

“Look up at me while I penetrate you, my sweet girl. This is your purpose now, and you should be happy to serve it. Your body will open for me whenever I demand it and you should get used to offering it up willingly.” He kissed my forehead, and my cheeks softly, then without warning thrust upwards and buried his long member deep into my small pussy. I gasped and clutched at Mr Charles’ broad shoulders; I could feel the pulsing tip of his penis pressing against my cervix and I was amazed by the intense sensation of intercourse without a condom. Small trails of precum and my own arousal ran down my labia as Mr Charles forced my vagina open wider, and I could feel his sweaty, slippery flesh pushing all the way inside of me with every thrust.

My labial lips were forced wide open and my legs were stretched as Mr Charles continued to thrust into me at a slow but regular pace. He kissed my face and my mouth and I could feel my pierced nipples grazing across his hairy chest. Suddenly he hitched my legs up onto his shoulders, bending me in half and tightening the grip of my pussy around his slimy shaft. On every smooth penetration, I felt Mr Charles’ bulging organ press fully into the depths of my vagina, forcing me open wide and making me gasp breathlessly with the combined pain and pleasure. I let out increasingly high-pitched squeals as my boss continued to pummel into me, slick sexual juices gathering on my pussy and thighs and dripping onto the bed.

Soon Mr Charles pulled out of me and roughly manipulated me onto my hands and knees. After a short pause I felt his penis pressing into my genitals again, and agonisingly slowly his bulbous cock head entered my vagina and pushed down towards my cervix. I could hardly contain my grunts of pleasure as Mr Charles penetrated me more deeply than ever before. He grabbed me by the tits and pulled me upright, clutching me tight to his chest so that I was bouncing on his cock as he knelt on the bed. In the large gilt-framed mirror opposite the bed I could see us, entwined together with my boss’ large hands groping my little pink breasts and my labia stretched open obscenely around his slick purple penis.

Sweat trickled down my neck as the speed of our mating increased until I was frantically jackhammering up and down on Mr Charles’ enormous sexual organ. I was completely consumed by lust and the repeated invasion of my genitals, along with sharp tweaks of my nipple piercings, was driving me towards a delicious climax. As my insides clenched tight around Mr Charles’ swollen erection, I groaned in ecstasy and felt my vaginal muscles ripple up and down his penis as I let my orgasm wash over me.

“You’re very responsive, my sweet girl. Well done. Now it’s my turn to cum, inside your slick little pussy. Take my semen; take it into your body.” With this, Mr Charles squeezed my torso even harder and stiffened, staying stock-still as copious volumes of ejaculate pulsed up his penis and sprayed into my grasping vaginal canal. I could do nothing but exist in my boss’ tight embrace as his semen flooded into me, completely covering my inner walls with hot, slick cum. Mr Charles released such a huge volume of semen into me that soon it was spurting out of me and dripping down my soft thighs, his huge cock not quite adequate to plug my vagina and prevent it from leaking out.

Although I was completely exhausted, after Mr Charles released me I lay back on the bed and as he watched I scooped his ejaculate out of my genitals and spread it over my nipples and lips. Leaning over, I carefully cleaned Mr Charles’ penis using my mouth, gently sucking away remnants of gloopy semen and running my hot moist tongue over the curves of his enormous cock. I giggled and traces of cum gathered at the corners of my mouth when I grinned up at my boss.

“Excellent. Rest now, sweet girl. We have a lot more to do.” I slumped back against the pillow, still leaking warm creamy semen from my stretched pussy, and soon fell asleep.

When I woke up, Mr Charles was sitting in an armchair in a bathrobe, and his eyes lit up when I looked over at him.

“You’re awake! Come quickly, sweet girl, and look out over the city while the sun sets. It’s so beautiful. I padded over, completely naked and blushing, and let Mr Charles stand behind me in the bay window, his hands on my bare shoulders as we admired the amazing evening view. Mr Charles leaned in behind me and kissed my neck and my earlobe. I felt him reach down between my legs and I squirmed when he inserted two fingers into my sore, swollen pussy. Hot semen was oozing out of my vagina and completely coated my soft bare labia. Runnels of the thick white fluid ran down my fleshy inner thighs, and Mr Charles let out a low whistle as he investigated my flooded genitals more fully.

“So much sweet ejaculate for you, my sweet girl. Well done, you have taken it very nicely. You have pleased me so far.” Something about the words “so far” made me shiver, and I was surprised when I felt Mr Charles’ hand at my face. He pressed his fingers into my mouth and I felt the viscous semen he had scooped out of my pussy coat my tongue.

“Taste it, my sweet girl. Taste us together. Open yourself to me.” I moaned and sucked his large fingers eagerly, my eyes clenched shut as I leaned back into Mr Charles’ strong chest. After a moment he pushed me forward until I was bent over the window sill, supporting myself on two outstretched hands. My small tits hung down and Mr Charles grazed my erect nipples with one hand while he forced my legs further apart with his knee.

“Stay exactly where you are.” I waited obediently, bent over with my seeping vagina displayed and I looked out over the skyline in a daze. Mr Charles had fetched a small bottle and caressed my soft fleshy ass as he smoothed sweet scented oil over my skin. Occasionally he would lean down and kiss my skin, then continue with his ministrations. I gasped when I first felt his finger trace my small tight anus, but I realised Mr Charles’ intentions at that point and resolved to do whatever I could to meet his desires. Slowly Mr Charles increased the pressure on my muscular anus until he had worked the tip of his index finger into my ass. He moved slowly and gradually, while stroking my body all over with his other hand, and I felt relaxed and surprisingly comfortable considering this was the first ever penetration of my ass.

When someone knocked on the door, Mr Charles called casually that it was unlocked. He must have felt me tense up, but with a strong hand on my shoulder Mr Charles made it clear that I was to stay exactly where I was.

“Hello – Oh!” The door started to close again as a hotel employee retreated, red-faced and with eyes averted.

“No it’s quite alright, what can I help you with?” asked Mr Charles, crossing to the door and holding it open.

“I wonder if… I thought this might belong to the young lady…” As he held up the tiny black thong we had left in the hallway, the employee was clearly torn between trying to be polite to Mr Charles and wanting to gape at my tight body bent over and spread open at the window. I could still feel sticky cum on my thighs and labia, and I knew the scented oil Mr Charles had been massaging into me had left my whole ass slick and glistening.

“Yes, thank you, it is. We were in a hurry earlier, I apologise.” Mr Charles graciously Accepted the lingerie in his upturned palm, then went on: “I’m glad you called in, actually – do you have two minutes to do us a favour?”

Looking dumbstruck, the employee stammered his agreement.

“Let me get straight to the point. Actually, it’s easier if I just show you.” Mr Charles led the employee over to the window and placed a hand gently on my upturned buttock.

“Tonight I plan to sodomise my sweet girl. She is of age and in agreement, of course, aren’t you?” I nodded and squeaked in confirmation.

“Please would you help us by holding her ass cheeks apart while I stretch her sphincter a little further? A third pair of hands would be really helpful. Like this, you see?” Without further ado, Mr Charles stretched my ass cheeks apart quite forcefully, until my ass crack was stretched white and my little ass hole looked looser than ever.

“Yes, quite like that, thank you.” Mr Charles turned his attention back to the lubricating oil as the hotel employee reached round and placed his warm sweaty palms on my skin.

“Even tighter, really pull her open for me, won’t you? I want to be able to see exactly what I’m doing.” said Mr Charles. I could see him behind me in the reflection of the window now that night had fallen. He had undone the bathrobe and was oiling up his enormous swollen shaft. The hotel employee seemed fixated on my slippery ass and dripping pussy and was staring at that until Mr Charles moved round and presented his shiny penis to my anal sphincter.

“Yes, spread her open for a moment and I’ll soon make my way inside.” Mr Charles pressed the tip of his huge member onto my anus and used his strong hips to push ever more forcefully against my tight virgin hole. He groaned slightly as he increased the pressure, and I could feel the stranger’s hands on my ass cheeks trembling. Mr Charles let out a sigh of relief as the head of his enormous purple erection popped past my anus and into my rectum. I let out a high-pitched squeal as I felt my inner canal readjusting to this large foreign intrusion.

“You can go now, you know,” Mr Charles said a bit sharply to the employee, who stood stock-still and mesmerised by the scene of this middle-aged man calmly taking his secretary’s anal cherry. I managed to wait until the door had shut behind him before letting out a guttural moan of mixed pain and pleasure. Mr Charles’ huge penis was slowly but surely slipping deeper into my rectum, and a swollen fullness was spreading through my lower half. Combined with my bruised pussy, I felt unbearably sensitive and vulnerable to my boss’ sexual ministrations.

“My wife refuses to take it up the ass you know, my sweet girl. She says only cheap sluts take cocks up their assholes. You’re doing me a real favour. So hot and tight!” My breath caught in my throat when I thought about Mrs Charles again but the continued invasion of my rectum was forefront in my mind. After several minutes of steady pressure, all nine inches of Mr Charles’ giant erection were buried in my anal passage, and his thighs were now pressed against my buttocks, with his pubic hair slightly tickling my ass cheeks.

“My sweet girl, you’re doing so well. Now I’m going to ass-fuck you properly. Remember the promises you made me.” Mr Charles abruptly withdrew his slippery organ all the way out of my body, then slammed back into me, causing me to lose my grip on the windowsill. As he continued his assault on my tiny sphincter, my whole upper body was pressed up against the window. Even my face, turned side on, was mashed into the glass as Mr Charles took his sexual pleasure from my virgin anus. If anyone happened to look up to the high window, my jolting naked figure, with breasts squeezed against the window and my pained expression of lustful concentration would have been clearly visible. My greasy asshole was looser now, and through the numbness I began to feel pleasure building. It was too late though: with a couple more sharp thrusts and a loud sigh, Mr Charles clenched his thighs and began emptying his testicles into my rectal passage.

Streams of his salty cream poured into my ass, sending shivers of warmth through my panting body as Mr Charles moved backwards and let his softening organ slip past my slippery buttocks. Cum slid down my inner thighs again, and Mr Charles wiped the final rivulets from his cockhead on my cheeks and lower back, bathing me in streaks of glistening ejaculate. He grabbed my neck suddenly and twisted my face around, then kissed me hard on the mouth, still slightly breathless from the exertion of our frantic sodomy. “Well done, sweet girl. You managed well. I’m proud of you.”

I had heard that older men took longer to recover after spewing their load, but Mr Charles had far more energy and stamina than any boys my age I had encountered. He fucked me hard four more times that night, in my engorged pussy and in my puckered anus, and his supplies of slippery semen seemed endless. I eventually fell asleep some time before morning, stiff and sticky from thorough sexual usage but more infatuated with Mr Charles as ever.

I was at home alone that evening when an unknown number rang my phone. I answered it tentatively.

“Good evening, this is Mr Charles’ driver. He has asked me to pass a message on to you: he will be dropping by briefly within half an hour with two work colleagues to whom he would like to introduce you. They are en route to a business dinner event but are running ahead of schedule. Mr Charles requests that you wear minimal clothing and that you lubricate your anus in advance. Do you have any questions?”

“No,” I whispered, my mouth dry and my heart racing. I jumped in the shower and shaved my pussy extra smooth, then squeezed copious lubricant directly into my rectum. The anal lubricant, in a bottle with a special easier pointed nozzle for anal injection, had been left in plain sight on my desk at work the day before. I massaged more lube around my small, tight anus, and rubbed warm scented oil into my breasts and over my skin. I pulled on a short, sheer nightgown, and due to my height it only skimmed my hips and left my pink labia on show. My nipple piercings had previously ripped the fine white lace so my nipples were left exposed through the resulting holes, and I pinched them slightly to ensure they were prominent enough to emerge through the nightgown, then settled myself nervously against a side table by the front door.

When Mr Charles let himself in with his own key, he whistled as he held the door open for two more middle-aged men. The way I had arranged myself, my labia were slightly splayed and the men could see my nipples through the ripped nightgown but also most of my pussy as it was spread open for them. I blushed furiously but stayed still until Mr Charles pulled me by the arm towards my bedroom and called to his companions to take a seat on the couch for a few minutes. In fact we never got as far as my bedroom: Mr Charles spun me round so I was bent face-first over a bookcase in the hall, quickly unzipped his pants and slowly but surely eased his large erect organ directly into my rectum. Regular anal sex had loosened my anal muscles enough that he could penetrate me immediately: all this had happened within about 90 seconds of Mr Charles’ arrival.

I groaned softly as I felt my young anus being opened and filled. I was so wrapped up in the pleasurable fullness that I did not realise the door to the sitting room was still open, and both Mr Charles’ business associates, now sitting on the sofa, had a perfect side-on view of what Mr Charles was doing to his twenty-year-old secretary in the hall. As he leaned slowly backwards, the two men could see my boss’s cock, glossy from the lubricant I had injected earlier, slowly pull out of my anus then drive quickly back in. Mr Charles had focused on the depth of penetration from our very first attempt at anal sex, and he still prioritised filling my anal passage to its depths over thrusting into me particularly quickly. Looking down, he pawed at my soft ass cheeks and held them apart as he watched his swollen organ invading my fleshy ass. I let out a high-pitched whine as I felt Mr Charles’ cock reach the very bottom of my rectum and his bulging testicles press into my soft smooth labia.

“You are so beautiful my sweet girl, and I am so proud of you. I couldn’t resist your little anus tonight but that’s not why I have come. I promise I will look after you.” Mr Charles grasped my chin gently, turning my neck and kissing my face and my lips. As his tongue entered my soft mouth I moaned gently and kissed him back, my rectum stretched and my nipples pleasurably taut. Then Mr Charles resumed his rhythm of thrusting as we kissed, my body twisted to allow him access to my anus and my mouth simultaneously as we stood leaning against the bookshelf. Just as I was feeling the stirrings of an orgasm, Mr Charles grabbed me tight and squirted hot cum into my rectum quite forcefully. I could feel the warm ejaculate splattering inside me and Mr Charles’ large sex organ twitching and spasming as it propelled more semen into my hole. He continued to hold me still and kiss my neck until his penis slipped out of my anus and warm ejaculate began to trickle down my legs.

“Well done, my girl. Very satisfying and compliant.” Only as I straightened up and tidied my hair did I realise the two other men had been watching the whole time. I gasped and, blushing furiously, moved to hide myself behind Mr Charles, but had already glimpsed their open-mouthed expressions and erections pressing through their pants.

“Surely you haven’t forgotten our agreement already, sweet girl? These are my associates and I have told them all about your lovely young body and how eager you are to please older men.” He took my hand and led me through to the living room, which also had a large dining table on the far side. I kept my eyes on the floor but I was secretly pleased that Mr Charles had been telling other people how satisfied he was by me. I allowed him to lead me to the table, then looked up at him, confused.

“Climb up on here, sweet girl. Let these men take a proper look at you.” I didn’t understand why the table was necessary but I sat up on it and allowed Mr Charles to push me down by the shoulders until I was flat on my back, with my head dangling over one side and my legs dangling over the other.

“You should decide who wants what now,” Mr Charles said to his business associates, who were now standing around the table looking down at me. The nightgown I had put on half an hour ago was gathered around my waist, fully exposing my bare pink pussy, and my nipples still poked through holes in the sheer material. As my head was dangling upside down, I could not see the looks exchanged between Mr Charles and the other two men before I heard two zips slide down and was faced with the erect penis of an unknown middle-aged man in close proximity. Mr Charles had taken a seat at the table near my head, his hand still pressing firmly down on my shoulder, and he gently stroked my face before turning it towards the other man’s cock.

“Accept this penis into your soft mouth now, sweet girl. You would do that for me, wouldn’t you?” I tried to shake my head and move away but now the other man took hold of my head too. As the stranger’s penis moved closer to my face, Mr Charles gently pushed a finger past my lips and hooked my mouth open for the penis to slide in.

“Good girl, sweet girl. You are doing so well. I am so pleased with your obedient behaviour. Keep your eyes open and look up at me, please.” Mr Charles looked down at me and stroked my hair and my face as the stranger thrust his cock into my mouth at an increasing pace. Just then I jumped and jolted almost upright as I felt pressure against my small smooth pussy.

“Yes, go on and penetrate her, she’ll be fine in a minute,” said Mr Charles to his other business associate on the other side of the table. “No condoms, sweet girl, because these are my friends and they deserve to feel your young body properly, don’t they. Spread your legs a little to allow him easier access, please.”

As one man’s penis slid back into my mouth and pressed its way down my throat, I automatically opened my legs and allowed another man’s bare cock to inch into my soft pussy. The feeling of bare skin pressed into me was still strange and I struggled to remain still as I was penetrated increasingly deeply at both ends of the table.

“Christ, Charles, she’s really tight. What age is she again?” asked the stranger whose erect cock was lodged tightly inside my vagina. I could feel his hairy thighs press against me as he thrust in and out, his average-sized cock feeling increasingly good inside my slippery little hole. My anus was still stretched and slimy from Mr Charles’ ministrations and my unfulfilled orgasm from that encounter was reappearing now.

“Just turned twenty, didn’t you my sweet girl,” he said, looking down at my stretched face, which was beginning to shine with sweat, drool and precum as the first man approached his climax.

“So that’s why you’re never available for a lunchtime meeting any more, then – you’ve found a twenty year old who takes it in all three holes!” The stranger whooped with laughter but there was a strain in his voice borne out in increasingly desperate thrusts of his penis into my tight vaginal canal. For the first time, the rhythm with which these two men were shoving their penises into my body was synchronised: every sharp thrust into my pussy pushed my convulsing throat farther along the second man’s veiny shaft, and when he pressed his organ most deeply down my gullet, my pussy was jammed forcibly onto the penis at the other end. As the pace increased frantically I grunted and drooled, my little tits jiggling in time.

“Go ahead and spunk inside her, boys. She needs to get used to it, really.” Before Mr Charles had finished his sentence I felt hot semen jet into my pussy. There was only a small amount compared to what Mr Charles regularly deposited inside my genitals, but in the circumstances and as Mr Charles tugged my nipple piercings with one hand, it was enough for me to orgasm briefly. Straight afterwards, the other man held my face with both hands and poured his semen into my throat and mouth, withdrawing quickly to streak a trail of gooey cum across my lips and chin. Mr Charles kept his hand gently under my chin, holding my mouth closed while I gulped down his associate’s salty ejaculation.

As I walked downstairs stark naked, my whole nubile body ached from its repeated exploitation the night before. Semen was splattered over my face, tangled in my hair and dried in rivulets down the sides of my mouth and onto my chin. There were also copious amounts of white cum splashed over my tiny tits and crusted over my small pointed nipples, with their silver piercings more prominent than ever. As well as huge spurts of semen dried over my smooth pink labia and peachy bum cheeks, I could feel warm, gooey remains of Mr Charles’ pleasure oozing out of my stretched vagina and dribbling down the inside of my thighs. Some streams had reached my knees, such was the volume of potent semen Mr Charles had propelled into my orifices the night before. I knew even more semen would be leaking out of me if it wasn’t for the smooth silver plug inserted neatly into my anal sphincter, which stretched my hole open for various erect penises but also acted as a stopper, currently sealing a large amount of viscous semen in my rectum.

I entered the kitchen and bent over to open the dishwasher and pull out a water glass. As I bent over though, I heard a sudden gasp and the thud of a bag of groceries hitting the tiled floor. I turned round to see Mrs Charles as the door to the kitchen, her face pale and shocked and outstretched arms empty. There was nothing I could do to hide my slutty naked self, crusted with her husband’s cum all over, and I realised that as I had bent over, Mrs Charles would have seen my large anal plug poking out from between my soft ass cheeks too.

Mr Charles’ driver was as professional and dispassionate as ever as he drove me to the doctor’s office. I had pulled on Mr Charles’ oversized shirt from the night before but apart from that my twenty-year old body was completely exposed. I clutched an ice pack to my forehead where the cell phone hurled by Mrs Charles had struck me. The immediate shock was subsiding already, but I was secretly extremely pleased by the concern Mr Charles had shown for my welfare when he tended me. Sending me to his doctor had the added advantage of getting me out of his marital home while his wife continued to scream obscenities and trash the furnishings in her jealous rage.

I was ushered straight into the doctor’s office this time, and came face to face with the same physician as before: the middle-aged man who had become painfully erect during my sexual health and contraception appointment. He eased the icepack away from my face and assessed the lump forming on my brow.

“There won’t be any lasting damage from this. Judging from your attire, you seem to have been caught in quite a compromising position. Maybe it could have been worse.” My cheeks burned and I knew he was right. My swollen and abused young form, coated in semen with a large anal plug protruding from my buttocks, must have been a huge shock for the prudish, middle-aged Mrs Charles. “While you’re here, we should do a health exam and check up. I know Mr Charles wants me to ensure you are exclusively intimate with him, so I’ll do some tests for sexually-transmitted diseases for evidence.” My head was aching now, and I let the doctor lead me to his examination table and slide the baggy button down over my pale shoulders.

“When did you last have intercourse?” he asked as he pulled on a pair of latex gloves.

“Last night. No, this morning. A couple hours ago, I guess.”

“Once? How many times?”

I paused. How many times had Mr Charles’ huge member forced its way into my tight body? I felt exhausted and finally sated so it must have been several. The doctor noticed my hesitation.

“I need an accurate answer. Start with instances of full vaginal intercourse, where semen was deposited in your vaginal canal.”

“Four, I think.” I mumbled. There had been so much semen, everywhere. Surely some must have been propelled towards my cervix.

“And as for anal intercourse?”

“Three times.” At least three times, I thought. With the silver butt plug reinserted immediately afterwards each time to maintain my anal girth and store up copious ejaculate in my rectum as future lubricant.

“Okay. Now lie back.” As the doctor probed my vagina with his gloved fingers, huge globs of creamy cum drooled from my labia and flowed out of my pink hole. It bubbled on my thighs and the doctor used several tissues to wipe it away so that he could continue his exam. I was resigned to his investigation now and let him spread my pussy wider to take his swabs and photograph my abused young genitals, covered in frothy spunk.

I heard the doctor let out a surprised chuckle when he realised shiny butt plug was shoved into my anus. He tweaked it slightly and my whole body jolted with remembered pleasure; I let out a choke of lustful surprise.

“I will do my best to take samples from around this device. I know Mr Charles prefers to manage their insertion and removal in some detail.” The doctor moved his cotton bud around the edge of my straining white sphincter then closed the sample in a sealed tube for testing.

“If you have engaged in oral sex, I will also need to swab your mouth. I remember from our first appointment that you enjoy receiving the male member in your mouth and throat?” I nodded hesitantly. “And you have actually allowed men to complete inside your mouth?” I nodded again. “Open up, then.” I stretched my mouth open and the doctor ran a final swab around the inside of my cheeks. He stored the swab and I was free to go. A black mood of disappointment and rejection settled on me as Mr Charles’ driver took me home.

“I’m coming over. P.” My cell phone buzzed with the text message and my head ached from where Mrs Charles’ hurled cell phone had hit me. I was nervous about what Mr Charles would be arriving to say, and in my anxiety, I had not noticed Mr Charles sign off his text with his initial for the first time – I expected his visit to last no more than ten minutes. He had taken care of me like he promised, but now was the end of this crazy affair with my boss: I was sure he would have mended his relationship with his wife by promising never to see me again. And this meant I had lost my job too: I really was just a silly twenty-year old. What had I been thinking? Even in my dejection and concern for the future though, I squirmed in pleasure whenever I felt more slippery cum leak out of my abused pussy. Although I had showered off the semen he had coated me in, I had left Mr Charles’ large butt plug in my anus as per his instructions, even though I knew he would probably go nowhere near it. My hair was damp and I was wearing an old t-shirt and a small cotton thong when I heard Mr Charles’ key in my front door: what was the point in dressing up to get dumped?

“My sweet girl! I’m glad you’re okay. I’ve been trying to get over here all day.” Mr Charles swept over to where I lingered by the kitchen counter and enveloped me in his strong arms. This was not the reception I was expecting, but I relaxed into his broad embrace and inhaled the sexy scent of the man I so desired. Leaning back but keeping me tight in his arms, Mr Charles tipped my chin up and kissed me gently on the mouth, softly at first but soon pushing his tongue past my lips. I melted into him and let him hitch my legs up round his waist, resting my ass on the edge of the countertop. I could feel his large penis growing inside his pants because it was pressing with increasing urgency against my thin panties. I leaned further into the kiss and opened my mouth wider, inviting my boss even further in and kissing him back passionately. After several minutes of arousing kissing, with Mr Charles’ hands roaming further around my nubile body and my heart rate increasing, I resolved to get some answers. Gasping for air, I pushed him back reluctantly and stared at his face.

“Why did you come? What did your wife say? Isn’t our arrangement over now?”

“Do you want it to be over, my sweet girl?” An expression of genuine upset passed across Mr Charles’ face.

“N… No…” I stammered, confused and with my heart still thumping from our intense make-out session.

“Let me deal with Mrs Charles. I’ll work it out. I have absolutely no intention of ending our agreement. If you ask me, my sweet girl, we’re just getting started.” He crinkled his eyes and smiled at me, then kissed my forehead. I felt incredibly vulnerable with my legs spread round him, butt plug clinking against the kitchen worktop, but I knew this was exactly what I wanted. The dominant, sexually-demanding side of Mr Charles was familiar to me but this nurturing approach was new – though equally as arousing. I nodded enthusiastically and threw my arms around his neck. Shuffling to get closer in to me, he pulled his cell phone out of the pocket of his suit pants and placed it on the counter. Glancing over I saw the photo set as his screen saver. It was a picture of me from the night before, glistening with his creamy semen over my face and pert breasts, laughing up at him as more cum dripped out of his softening penis onto my face. I felt so happy and proud that Mr Charles had chosen this sluttish image of me, coated in ejaculate and utterly under his sexual thrall, to see every time he looked at his phone. And I knew that underneath the practicalities of our sexual arrangement, Mr Charles did hold true affection for me, his petite twenty-year old secretary.

“I never stopped following your instructions, Mr Charles…” I whispered into my boss’ ear. He drew back and looked at me quizzically, so I took his hand and guided it down to where the silver metal butt plug poked out of my taut anus. He raised his eyebrows and looked very pleased, then lifted me off the counter and walked us over to an armchair where he settled me down on his lap, and began to kiss me gently again. I responded instantly and felt myself getting aroused, and I stretched my neck back to kiss him more forcefully. His hands stroked gently over my waist and pushed up under my t-shirt, and he began to massage my small breasts and twist my nipple piercings teasingly. I tried to twist round and straddle him but stopped me and held me still, sitting sideways across his lap with his prominent erection jutting into my soft thighs.

“But, Mr Charles…” I pleaded softly as I again tried to shift myself round towards him.

“Call me Peter now, sweet girl. Or daddy,” he chuckled to himself. “After your long day I won’t demand anything. But I would love to fill that sweet asshole with cum. Would you like that? Will you let me fuck your ass?” I shivered with lust and pulled his head down for another intense kiss.

“Of course. Tell me what you want. Tell me what to do. My body is all for you.” I lifted my t-shirt over my head and let Peter quickly rip off the thin thong so I was naked. Agonisingly slowly, he repositioned my body so that I was kneeling over him, my shins outside his thighs, facing outwards from the armchair and with my young form stretched open opposite the front door. I leaned forward and after Peter had removed his huge erection from his pants, he kissed my ass cheeks gently and massaged my soft flesh. Soon I felt him gently twisting the large anal plug and my intense lust masked the discomfort as the sizeable metal object popped out past my recently defiled sphincter.

Peter immediately guided me down onto his stiff penis and sank himself into my convulsing anal chute, using his previous semen deposits as creamy lube. Around my stretched asshole remnants of semen leaked out and covered my ass and Peter’s groin in sticky cum. I let out a guttural moan as I sank backwards onto my boss’ large member, revelling in the sensation of my rectal passage being stretched and filled so satisfyingly. My inner muscles clenched and rippled along Peter’s shiny shaft as he gently penetrated me to the hilt. His hands reached up and caressed my heaving tits as I settled into a rhythm of slow and pleasurable ass-fucking. I was consumed with desire and relief that our arrangement – now bordering on a real relationship – was safe for now. I would continue to allow my boss constant access to my young body. His cock reached so deep inside me that an orgasm was stirring very quickly, but I kept the pace of anal insertion slow and steady to draw out the pleasurable sensations. Peter’s big hands roamed all over my tight twenty-year old body as his nine-inch cock ploughed my clenching asshole over and over. He especially enjoyed squeezing and manipulating the soft fleshy globes of my ass as his swollen sticky shaft eased in between them repeatedly.

“My sweet girl, you have such a fantastic ass. Thank you for letting me enter it. Thank you for giving me control of it. I love having control over your sweet tight body.” I moaned again as Peter’s whisper tickled my neck and I felt his hand slip round to massage my clitoris. With every upward and downward movement I made on his huge stiff cock, my boss’ hand stoked my orgasm further by careful stimulation of my slimy bald pussy. At the final climactic moment I squealed and sank down as far as I could, forcing Peter’s erect cock to penetrate my slippery young asshole deeper than ever as I clenched and shuddered in orgasm. I felt no pain but only extreme pleasure as my tiny anus, stretched white around Peter’s considerable girth, pulsed and quivered, and I panted and squeaked with intense sexual satisfaction.

Just then, my stomach lurched as I saw the front door pushed open. In his haste to greet me, Peter must have left it a tiny amount ajar. I could barely concentrate on the door as my creamy anal passage continued to ripple intensely and my tits quivered and tingled from Peter’s massage. My wide stance on the chair spread open my bald pink pussy and showed clearly where my boss’ hand was tickling my clitoris to orgasm, surrounding my dripping spunk from repeated use and abuse by Peter. I stared on helplessly as my college boyfriend took in the scene, standing at the front door in his raincoat with a bunch of flowers in his hand. I could not even speak to him but only gasp as I felt Peter’s climax begin and the warmth of his squirting cum deposit start to spread deliciously through my lower abdomen.

“I… I can’t stop now… Go away, you don’t need to see this!” I managed to enunciate a few words in my boyfriend’s direction as Peter’s creamy ejaculate spurted into me, and his strong fingers continued to waggle deliciously over my pink pussy. But my boyfriend stood there, transfixed, as my middle-aged boss violated my anus with my own eager permission. Gentle pressure on my thighs prompted me to lean forward gently and I screwed up my face in intense enjoyment as all of Peter’s stiff shaft slowly emerged from my rectum. Peter stroked my back as he nonchalantly reached across and retrieved the butt plug, then popped it past my sphincter using his most recent plentiful ejaculation as slippery natural lubricant. Some of my boss’ precious cream shone obviously on my soft inner thighs as my boyfriend looked on, but I knew plenty was also stored up inside my clenching ass canal for future erotic fun.

It was Saturday morning, and since I had forced my college boyfriend to move out I was alone in my flat with no particular plans for the day. I drew a bath and relaxed in the hot water, letting the bubbles drift over my pert little tits and stroking my flat stomach absent-mindedly. As well as my legs and armpits, I shaved my tight snatch completely to leave it pink and bare. I had no idea when I would see Peter next but I wanted to make sure my young body was ready for whenever he wanted me. Thinking of Peter, my small hand wandered down to my hot clit and I started rolling it between my fingers, imagining it was my middle-aged lover instead. I had been on an incredible journey of sexual discovery over the past few weeks and my awakening was all thanks to him. Leaning my head back, eyes clenched shut, I came on my hand, picturing Peter pressing his thick cock past my lips and deep into my convulsing throat.

Just as I climbed out the bathtub, my phone rang and my heart leapt.

“Hello, sweet girl. What have you been doing this morning?”

“Hi daddy, I was just in the bathtub, thinking about you,” I blurted out without thinking. He chuckled and pressed me for further details. “Um… I, I was touching myself. And imagining it was you.” My face burned red but I was also getting aroused again explaining to my middle-aged boss how horny I was for him. “I like it when you ejaculate in my mouth and throat.”

“Oh my sweet girl, I like that too. Very much. But I have so much work to do today. Can you come to the office and help me get through it?” I agreed instantly. “No one else will be around, so no need for office dress. Just be comfortable.” We hung up and I began to get ready. I pulled on a short white summer dress, which was relatively high-necked but had buttons running all the way down the front, from the neckline to the hem. A bra would have shown under the fine straps so I didn’t wear one. I had intended to pull on a pair of panties but my only clean pairs were bright colours which would have shown up under the white fabric of the dress, so I left those off too, with an excited flutter in my stomach. I pulled on a pair of plimsolls, left my soft, shiny hair loose down my back, and headed to the office.

Peter was at his desk when I got there but the rest of the building was empty. I opened his door shyly without knocking, and watched him concentrating on a bundle of documents. He was wearing a simple white button down with jeans and I thought he looked incredibly handsome. The outline of his strong arms showed clearly through his shirt and he had a shadow of grey stubble across his well-defined jaw.

“Hi,” I said in a quiet voice. For some reason I still felt like no more than a shy teenager whenever I approached this powerful man, despite him having entered and used my body countless times. He looked up and his face broke into a genuine smile.

“Hey baby, I’m glad you’re here. Whoever drafted these documents had no idea what they were doing.” I sidled over to his desk and as I looked over the documents he was talking about, he stroked my thigh gently under the sundress. “You have such beautiful soft skin.” His gentle fingers roamed gradually higher and higher, and I realised with a start what he was expecting to find. “No panties, my sweet girl?” he asked with obvious amusement. “What did you expect we would be doing this afternoon?” I turned bright red and tried to explain about my laundry situation. “I’m not sure about this sluttish behaviour at work. Perhaps disciplinary action is required.” I started to protest but I saw the twinkle in his grey eyes and decided to play along. “Turn around and lean over the desk, sweet girl. I’m going to enjoy this enormously.”

I did as I was told and I felt a breeze over my bald genitals as Peter lifted my skirt and rearranged it over my back to leave me properly exposed. Standing behind me, Peter squeezed and caressed my soft ass cheeks, moulding them to his palms and tickling my inner thighs with tantalisingly gentle strokes. Suddenly I shrieked with pain and surprise when Peter’s hand landed with a very sharp spank on my ass cheek. I felt my whole ass jiggle with the impact and there was a hot sting on my young peachy skin where his palm had landed. Before I could turn around, another spank landed on my other ass cheek, and another, until Peter had fiercely spanked me eight times. My whole ass was stinging and swollen; Peter had spanked me so hard I was sure my twenty-year-old skin would be bruised. I had barely had time to cry out again, never mind protest, but I tried to face Peter now and he held me still against the desk, facing away from him. I felt his erect cock pressing into me through his pants and it felt bigger and stiffer than I had ever known it. Still holding me in place, Peter sank back into his desk chair behind me.

He immediately leaned forward and began kissing my sore red skin, gently at first but increasingly enthusiastically, sucking on portions of my jiggling ass and making me giggle with the soft popping noises. The careful attention my boss was now paying to my sensitive ass was well worth the earlier spanking, and I settled lower on the desk so I could graze my stiff nipples over the wood through my sundress. I groaned when I first felt Peter’s tongue burrow into my flushed pink pussy and slowly stroke towards my engorged clit. He administered his sucking and kissing so gently and tenderly towards my hairless labia and slick folds that I was soon writhing under him in lustful pleasure. I could hear his lips smacking against my sweet bald pussy and he seemed to savour the runnels of arousal dripping out of my sexy snatch. Pulling my ass cheeks apart with his large hands, he made more space for his face between my legs and rubbed his tongue, mouth and nose over my most sensitive genital areas.

“You’re delicious, my sweet girl. I’m completely captivated. I need you now.” Peter pulled me round to face him at the same time as he pushed his jeans down to around his knees. My dress fell back down and he gently unbuttoned it from top to bottom, so it was entirely open at the front and my whole quivering nude form was available to him. He leaned back in the chair, opened his legs and tapped on his thigh, inviting me to straddle him. I climbed on, rubbing my sweet little tits in his face and feeling his stubble scratch over them pleasurably. Peter’s huge cock was so hard I didn’t even need to reach down for it with my small hand, but simply sank downwards and felt it meet my pussy directly. His fat purple cockhead split my juicy labia first, then popped into my tight canal and travelled upwards to meet my cervix, as the whole wide shaft stretched open my young vaginal passage. Peter reached round and supported me softly under my tender bruised buttocks, so I could bounce gently up and down on his slick, engorged sex organ.

We were not occupied with much thrusting yet, but merely enjoying the incredible sensation of such deep penetration and intimate closeness. Peter kissed me lightly on the lips, then leaned in and held my neck for a much longer kiss. I wrapped my arms around his neck and responded in kind, massaging my tongue against his and rubbing my soft lips over his handsome face. I felt Peter’s kisses trail across my jaw and down my neck before he returned to my mouth for a deep and lingering kiss there. I rested on his lap, speared by his enormous organ, my dress wide open and his jeans round his knees, for what seemed like hours, revelling in our steamy make-out session. For a long time Peter seemed entirely content to kiss my young face and tease my tongue with his, stroking my back and nibbling my earlobes intermittently.

“You know I genuinely was planning for us to do work today,” he said quietly. “I can’t resist you, though, and knowing your sweet tight pussy was bare under your dress was too much.” He laughed and stroked my hair. “This doesn’t feel like an arrangement to me anymore. I suppose we’re getting close to making love.” At that, my vaginal muscles clenched around his shaft involuntarily, and he knew how I felt. Almost overcome with both emotion and lust, I had to start bouncing on Peter’s thick cock again. I did so gently but relatively quickly, and we continued to make out sloppily as Peter’s slippery big cock stretched its way in and out of my inexperienced love canal. I only withdrew from our kiss to take gasps of air as I edged towards an earth shattering orgasm. Previously Peter had always ended up fucking me pretty violently before he climaxed in my pussy, but I saw a furrow of concentration appearing on his brow now too. My soft thighs were slimy with my arousal and Peter’s precum as I continued to gyrate on his lap breathlessly and I moaned into my boss’ open mouth as my young pussy began to spasm in an all-consuming orgasm.

Just at that point, Peter groaned quietly too and held me tight against him as we kissed, his solid sex organ tensing inside me as it began to spew out its hot, stringy gift. As we kissed and panted, Peter’s creamy semen flooded into the depths of my tight love canal, propelled towards my cervix and coating my rippling vaginal walls with delicious goo. I felt viscous semen gathering around my labia and I shuddered in pleasure as the gummy mixture of our juices slipped across my clitoris. I held onto Peter tight as his balls continued to pulse and thick ropes of salty sperm squirted into my young body. He held me close, with our sexual organs still closely joined, and we kissed and snuggled and cuddled for much longer.

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Young woman enters unusual arrangement with powerful boss.

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