Unprotected 3
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He was right about me being sore though. That one thick finger he’d fucked me with had left my pussy feeling stretched open and raw in a way I’d never experienced before. When Mr. Phillips finally let me ride his dick, I probably wouldn’t be able to walk the next day.
I’m not ashamed to say that the thought of being fucked bow-legged made me even wetter.
Two days had passed, and Mr. Phillips hadn’t given me any indication that he was ready to take things further, so I decided to take matters into my own hands.
I knew he wouldn’t agree to fuck me unless I proved that I could take his dick. I didn’t have any sex toys, but I did have a well-stocked fridge. I opened the crisper drawer to see a bright green cucumber waiting for me. It was about six inches long and nowhere near as thick as Mr. Phillips’ cock, but it was definitely a start.
I had called Mr. Phillips earlier and left him a message with my address and a request to come over at 5:30. It was just after 5:20, and Mr. Phillips was always on time, so I had to be ready. I left the front door unlocked, took off all my clothes and sat down on the couch. I stared down at the cucumber in my hands, still cool from the fridge, and I opened my legs.
My pussy had been in a constant state of arousal since the first time Mr. Phillips touched me, so when I pressed the cucumber to my slippery hole, it slid right in.
“Oh,” I gasped, a little shocked at how incredible it felt. The cucumber might not have been close to Mr. Phillips’ cock in size, but it was a lot thicker than his finger had been. I pushed it in, deeper and deeper until I felt it hit my barrier. I wanted Mr. Phillips’ cock to be the thing that split my cherry open, so I contented myself with just that little bit of penetration.
Ever so slowly, I started pumping the cucumber in and out of my pussy, stretching my tight hole as the pleasure built in me. I heard the front door open, and I let out a little gasp, alerting Mr. Phillips to my location. I couldn’t wait to see his reaction.
I looked up to see him standing frozen in the doorway, his eyes focused between my legs. Snapping out of his surprise, he asked, “Is that a. . . cucumber you’re fucking yourself with?”
“Yes, sir,” I breathed, watching my pink pussy lips stretching around that thick green vegetable. “You said we needed to stretch out my little pussy for your dick. So that’s what I’m doing.”
Mr. Phillips laughed, and I could see that the front of his pants was already growing tight. “I did say that, didn’t I?” I gasped, feeling myself getting closer and closer to coming with each of those shallow thrusts. “Not yet,” he ordered, grasping my wrist and stilling my hand.
Mr. Phillips pulled the cucumber out of my body and held it in front of my face. The long, green cylinder glistened with the fluid coating it. “Open your mouth,” he ordered. I hesitated. “Open your mouth,” he repeated, more insistently, pressing the sticky vegetable against my mouth.
Obediently I opened my mouth and found it filled with the hard, unyielding cucumber. The sweet and salty taste of my arousal spread across my tongue, mixed with the cool, green taste of the vegetable.
“Bite down,” Mr. Phillips demanded. “Only greedy little children waste food. If it’s good enough for you to fuck yourself on, it’s good enough for you to eat.”
My cheeks blushed hotly as I bit down on the vegetable, the clean taste exploding across my tongue. I tried to pull back after the first bite, but Mr. Phillips pushed more of it into my mouth. “You’re going to show me that you can take it all,” he said, pressing the cucumber deeper into my mouth.
I swallowed more and more of the vegetable, biting off chunk after chunk. The thin juice dripped down my face, the same way Mr. Phillips’ come had coated me only a few days ago.
While one hand made sure my mouth was busy, the other found it’s way between my legs. The single finger was replaced with three, and they scissored my pussy apart, stretching those innocent pink walls, getting them ready for his anaconda.
“If I had known you were so horny you’d fuck yourself on produce, I’d have taken you when I first hired you,” Mr. Phillips said, his thumb rubbing against my clit.
The last inch of the cucumber was in my mouth and I swallowed it down with the same eagerness I’d taken Mr. Phillips’ load a few days ago, and he slipped a fourth finger inside me.
“Do you like that?” he asked, as I watched his fingers disappearing inside my little pink hole. “Do you like knowing that you’re finally going to feel what it’s like to have a cock inside you, filling you up with the most intense pleasure you can experience?”
Ever since I had caught that glimpse of Mr. Phillips naked, I’d been consumed with lustful thoughts about him. I’d listen to his forceful voice at a meeting, and I’d imagine him growling dirty words as he plowed me with that thick cock. I’d sit across from him, my pussy dripping, and imagined sucking his dick until he came all over my face.
A few weeks ago, I’d felt daring, and I’d slipped my finger under my skirt and between my legs, masturbating silently while staring at Mr. Phillips through my open office door. My finger had pressed against my clit through the thin fabric of my panties and I’d come in less than a minute, hiding my shivers behind a sneeze.
As if reading my thoughts, Mr. Phillips spoke up. “I knew you were touching yourself that day, you know.” He pulled his fingers out of my pussy and I whimpered at the emptiness. Mr. Phillips stood up and unzipped his pants, pushing them to the floor and hurriedly stripping off his shirt, baring all 6 feet 5 inches of sexy tan skin to my eyes. “I knew you were fingering your little pussy right at your desk. I could smell it, and you weren’t fooling anyone with that fake sneeze when you came.”
I stared at his dick. Impossibly, it seemed to have grown even larger since the last time I’d seen it. “You made me so fucking hard, I almost broke my zipper.” Mr. Phillips laid down on top of me on the couch, and the head of his cock pressed between my legs, the blunt head butting up against my opening. "As soon as you left I went into my office and jerked off, but it wasn’t enough.” Mr. Phillips paused, his brown eyes staring into mine. “I didn’t want to wrap my dick in my hand. I wanted to bury it inside you.”
He pushed forward ad the head of his cock slipped inside my opening, feeling impossibly huge already. “Fuck, that’s it,” he growled, pushing in deeper. “Such a nice tight little pink pussy you have.”
Four fingers hadn’t been enough to ready me for my boss’ snake. I felt like my pussy was being split in two. It hurt, but I couldn’t imagine telling him to stop. Instead, I stared down at the spot between our bodies where we were joined, mesmerized by the sight of my pink lips wrapped around his staff. He wasn’t even halfway inside me!
I felt Mr. Phillips’ dick hit the thin barrier inside me. “I didn’t quite believe you were a virgin until I felt this,” he said. “Your boyfriend was a little bitch. If you’d been my girl, I wouldn’t have waited this long.”
“Then take me, sir,” I groaned, bucking my hips upward. “Pop my cherry.”
Mr. Phillips’ lips curled into a dirty smile, and he slammed forward, ramming his dick into me to the hilt and tearing my virginity in two.
I cried out in pain. As huge as Mr. Phillips’ dick had looked hanging between his legs and as big as it had felt filling my throat, that couldn’t even begin to prepare me for the way it would feel plowing into my pussy. After that first thrust split me in two, Mr. Phillips held still, holding himself up on his powerful arms.
“You okay?” he asked. The burning pain between my legs was beginning to give way to pleasure and an incredible feeling of fullness.
“Yes, Mr. Phillips. I told you I could take every inch.”
He chuckled, the slight movement shifted his cock inside me and we both gasped.
“So fucking tight,” he growled, and Mr. Phillips started thrusting. I felt every pounding thrust from my pussy all the way to my teeth. He had definitely ruined me for regular boys. No dick other that his would ever be able to fill me up now.
“I can’t hold out much longer, baby girl,” The billionaire said, his jaw clenching with the effort of holding back. “Your pussy’s just too tight and too hot, but I want to feel you squeezing my dick before I come in you.” He kissed my ear and added, “I can’t wait to see what you look like with my come running down your thighs.”
Like a freight train, my orgasm slammed into me. Every part of my tightened up and Mr. Phillips let out a yell as my inner walls grasped his cock like a wet fist. I felt a rush of heat as his come poured into me, but I barely registered it. My whole body was quaking in the most intense pleasure I’d ever felt.
As an afterthought, I realized that we hadn’t used any protection. Mr. Phillips’ come had absolutely flooded me, and I knew very well that it only took one time to get pregnant. Oddly enough, I found myself not caring. I didn’t even know if Magnum condoms would fit his dick, and the thought of having a layer of rubber between us wasn’t appealing. I’d take my chances, and if Mr. Phillips got me pregnant, that would just mean my breasts would get bigger. I bet my boss would like that.
Mr. Phillips slumped on top of me, crushing me with his larger frame as he caught his breath. I hissed as his cock slipped from me. He stood up and paused, staring at me. What a picture I must have made with my legs spread and his come dripping out of my well-fucked pussy.
“I don’t think you’ll be teasing those boys anymore, will you Janine?” He asked, dressing slowly.
“No, sir,” I replied, gingerly sitting up.
“It’s too bad I have to go out of town soon. You still have one cherry left.” My eyes widened at the thought of that huge dick going inside my ass, but I couldn’t hide my curiosity either. If other girls could do anal, so could I!
***
“I want you to fuck my ass.” Mr. Phillips was leaving in a few hours for an evening flight to Tokyo. He’d be gone for two weeks, and I wanted to make sure he had plenty to remember me by when we were apart. My pussy was still way too sore for another round, but we had other options.
“I don’t think your little ass can handle all of me, Janine,” Mr. Phillips protested. His protests rang hollow though. His hand had already dropped below his waist to massage his growing erection.
“I know it’s going to hurt, but I don’t care.” I unfastened the robe I was wearing and dropped it to the floor, standing naked in my kitchen. I walked over to the kitchen island and bent over, giving my boss a clear view of my ass. In seconds, he was standing behind me. With his free hand, Mr. Phillips unzipped his pants and I moaned as I felt the length of his cock sliding along the cleft of my ass.
“I need to put my fingers inside that hole first and stretch you until you can take my dick. You’re going to be so tight, Janine, even tighter than your pussy. And your pussy was like fucking bands of steel around my dick.”
Mr. Phillips grabbed the bottle of olive oil sitting on the counter. I watched over my shoulder as he slicked up his fingers, pausing as he pressed them at the tight pink bud of my anus before pushing into that untouched opening. I whimpered at the incredible sensation of fullness from just one of his fingers.
I looked at my reflection in the window over the sink and stared at myself and the wonderfully dirty image of my billionaire boss fucking my ass with a single finger. As I watched, he added a second finger and began spreading them apart inside me, loosening the tight muscles to prepare me for his dick.
He poured a generous amount of the slippery oil in his palm and spread it over his dick, hissing in pleasure from the touch of his own hand. Without asking me if I was ready, he lined the blunt head of his cock against that tight hole and thrust inside.
It was nothing like when Mr. Phillips had slipped easily into my pussy. Only the head of his cock had made it past my rim. Luckily my boss was a very patient man.
I grunted loudly as Mr. Phillips filled me up, but I kept my eyes riveted on our reflection in the window. He pushed inside of me, inch by inch. My fingers dug into the countertop as I tried to breathe through the incredible feeling of fullness. Mr. Phillips had only pushed about half his cock into me when he pulled back and started thrusting. My breasts bounced with every jarring thrust, and I felt almost like a dog in heat as he pumped inside me. My pussy tightened at that filthy thought.
“You’re so tight,” he ground out. “I can’t even fit my whole cock inside you, but that just means we’ll have to practice. I’m not going to last long in that ass. Touch yourself, Janine. I want to feel you come.”
I was surprised how much Mr. Phillips fucking my ass really had turned me on. When my hand dipped between my legs, I found a flood of my pussy juices soaking me halfway down my thighs. I found my clit between my swollen lips and started stroking while he continued the shallow thrusts in and out of my ass.
I couldn’t look away from our reflection in the window. My hand was between my legs, furiously fingering my pussy while my boss fucked me in the ass. I looked thoroughly slutty and nasty as I let him do whatever he wanted to my body, and it just turned me on more.
My orgasm hit me hard and every muscle tightened. My ass squeezed Mr. Phillips’ cock like a vise, and he let out a yell as he emptied his come in me. He pressed against my back for a few long minutes, trying to get his breath before gingerly easing his cock from my well-fucked ass. A trickle of his seed poured out of me, leaving a white streak down the lower curve of my ass.
“Are you happy now, beautiful?” he asked, smacking my ass playfully.
I smiled. Despite all the soreness, I was. I’d finally gotten my wish. I’d tamed that thick snake with my mouth and my pussy and my ass. I couldn’t wait for my next taste!
***
All those scare tactics they use in middle school health classes proved to be right. I ended up getting pregnant from the first time I had sex.
I was luckier than most women. I didn’t have any kind of sickness at all. The only difference I noticed was that I was even hornier than usual, which was saying a lot.
Mr. Phillips was gone for almost two months on his work trip, and all we had was video chat to keep each other satisfied. I spent about an hour every night naked in front of my computer, spreading apart my legs and fucking my fingers into tight pussy while Mr. Phillips watched. But it was never enough.
My boss was actually the one who figured it out. He had been back for a week, and we’d had sex at least twice a day. I couldn’t get enough of his dick, and it took almost nothing to make me come.
We were sprawled on his bed, sticky and exhausted after round three. My legs were spread wide, his come staining my thighs and Mr. Phillips ran his hand over my flat stomach. Except it wasn’t completely flat anymore.
It was just a little swell, but it was definitely there.
“Janine, I think I knocked you up,” he said, awe in his voice. “You’re so horny I can hardly keep up, your belly is a bit swollen, and-” he paused, looking up at my breasts. They had definitely grown. I was already spilling out of all of my bras. “Your tits are bigger too. You’re pregnant!”
If I had been worried at all that Mr. Phillips would be unhappy, that disappeared. An instant later, I found myself flat on my back again, Mr. Phillips’ renewed erection slamming into me.
“I can’t wait until you’re huge,” he growled, his dick pummeling my well-fucked pussy. “I can’t wait until your belly is enormous and your breasts are swollen with milk. Fuck!”
And he was true to his word. The bigger I got, the more Mr. Phillips wanted me. By the time my belly had really popped and my breasts were overflowing with milk, my boss was insatiable.
When I say “overflowing with milk” I mean it too. My milk had come in
early, and for some reason whenever I got aroused my pussy wasn’t the only thing that ended up wet. When I got turned on my nipples grew hard and my milk started dripping out of them. It wasn’t a lot, but it was enough to soak through whatever bra I was wearing. Even if I wanted to hide how turned on I was, I couldn’t.
Mr. Phillips absolutely loved it.
I’d be sitting in his office, trying to work but thinking about how I wanted to be bouncing on his cock instead. I’d feel the dampness growing between my legs and think nothing of it, but a few minutes later I’d have two wet spots on the front of my shirt. Then a few minutes later I’d find myself on top of the nearest flat surface, Mr. Phillips pounding into my pussy.
Except today. Mr. Phillips was working on quarterly reports and doing his best to ignore me where I sat working on department memos. The light blue dress I wore clung to every curve, emphasizing the huge round swell of my belly. My mind idly strayed back to last night where I’d sucked Mr. Phillips’ cock until he was ready to blow and then laid back as he painted by belly with come until I was a sticky, pearl-colored mess.