“Oh fuck yes, Sara,” he breathed, his head lolling backwards.
It seemed that the head was by far the most difficult part to get into my throat, once that was in, paving the way for the rest, inch after inch of his length disappeared past my lips until my lips came to rest at the base of his dick. I stayed there for as long as I could before pushing backwards because I needed air.
For a second Mr Warren’s hand kept forcing me down and I felt a surge of panic but then he let me off and looked up at him as I breathed heavily.
“I did it!” I exclaimed and then blushed.
“Good girl, Sara.”
“Is this enough?” I asked, half hoping that he would say he wanted more, half ashamed of the betrayal this meant to my boyfriend.
“No, Sara, you need to let me cum in your mouth.”
“Oh.”
I didn’t even bother protesting anymore, I realised I wanted to have him cum in my mouth, the ultimate experience of what a real man tasted like. His cock was so much bigger than my boyfriend’s, I bet he came loads more than that drop I had seen in the end of my boyfriend’s condom when we had sex. Without prompting or pushing I lowered my mouth back on to his cock and began bobbing up and down of my own free will.
“Get your knees up on the seat, it will help with the angle.”
I did exactly what he told me to do, ending up with my face in his lap, my knees on the seat and my ass up in the air. If anybody had walked past my side of the car at that moment, they would have seen my short schoolgirl skirt barely covering my cheeks. Mr Warren sensed the shift in my behaviour and let go of my hair, reaching over to flip my skirt up over my back and pulling my panties down to my knees. The view for any passers-by improved dramatically I guess.
He was right, though, having my knees up on the seat made it way easier to suck his dick and I did so without any care for who might see my pussy. My only concern in the whole world at that point was to get that cum inside my mouth, I wanted it, I needed it. How had me made me his little cumslut so easily?
I attempted to take his entire length again and felt the head hit the back of my throat and my muscles clenched up, I couldn’t get it in. He sensed my difficulty and gave my head a firm push, forcing his erection past the most difficult part. If my throat hadn’t been blocked I would have sighed in relief. It was wonderful having that thick meat slide down my neck, I felt so accomplished.
Mr Warren reached around one of my thighs and began stroking my clit from behind. I moaned as best I could as my lips once more found the base of his cock. I swirled my tongue all over his shaft for as long as I could, but his manipulation of my most sensitive spot made me breathless and I couldn’t keep it embedded in me for as long as the first time.
I pulled up and felt the head re-enter my mouth. I took it out, kissed it and then reinserted it, caressing it all over with my tongue as I felt my second orgasm approaching. I moaned louder and louder, beginning to buck my hips against his flickering finger.
“Do you want me to make you cum, Sara?”
“Yes, oh fuck yes please, Mr Warren.”
“You can cum again if I can fuck you.”
He stopped moving his finger on my clit and I was tortured with how close I had been. I must have lost my mind because I forgot my misgivings about being able to fit him inside of me and instead consented to what he wanted.
“Anything you want, Mr Warren, just… please!”
“Climb on over here and straddle me.”
Mr Warren reclined his seat as I climbed over him, my panties first fell to my feet and then off my left leg completely, remaining bunched up on my right ankle. I put a knee down on either side of his hips and grasped his cock with one hand.
“Do you have a condom?”
“A condom?” he looked at me like I’d asked if he had a dinosaur.
“I’m not on the pill, we need a condom.”
“I’ll pull out, just be ready to jump back over there so I can cum in your mouth, just like I said I would.”
“Are you sure?”
“Yes, now get that cock in your little pussy and stop talking back.”
“Oh… OK… just remember to tell me when.”
His dick was still in my hand and I guided it to my entrance as I lowered myself down. The feeling of it pressed up against my only recently deflowered pussy brought me partially back to my senses, regardless of how close my orgasm was.
“It won’t fit, Mr Warren.”
“Yes it will, baby, just keep pushing, put your weight on it.”
I gulped and did as he said. Our slippery genitals pressed together with more and more force until I gasped and felt my pussy lips part for him, accepting most of the head inside me, where only my current boyfriend had been before. My lips stretched outwards and I felt them close again against his shaft as the fat head made its way completely into my nearly-virgin slit.
Just like deep throating that was the hardest part and, thanks to our mutual slickness, his cock made steady progress into my depths. It wasn’t long before there was no more cock to slide in and my pussy lips rested at the base of his shaft where my other lips had been only minutes before.
“I told you it would fit Sara, good job. Your pussy feels fucking amazing.”
“Thanks Mr Warren.”
There was something about having him praise me that made me feel so proud of myself, I was giving this much more experienced man pleasure and it was an incredible, and admittedly odd, boost to my self-esteem. I smiled at the compliment and began riding his cock, desperate to return to the wonderful realm of climax.
Mr Warren began thrusting upwards, meeting my downward motions with a slapping sound that sent vibrations to my clit. I’d never felt anything like his cock in my pussy before, it was fantastic. When I was a virgin I’d stuck the handle of my hairbrush up there when I masturbated, then of course my boyfriend had fucked me, but Mr Warren’s cock and my slit were made for each other I decided as my orgasm quickly built up again.
Suddenly I felt myself fall over the edge of ecstasy as my orgasm washed over me. My legs quivered uncontrollably and I couldn’t ride Mr Warren anymore, I collapsed forwards and wrapped my arms around his neck like I was holding on for dear life. It seemed that was almost true, actually, my pleasure was so intense that I almost blacked out. Vision went fuzzy and sounds seemed to come to me from a distance.
Vaguely I felt Mr Warren wrap both arms around me, crushing me to his chest, and he began thrusting upwards quick and hard like a jack hammer. Such was the power of his thrusts that even my little tits shook on my slim frame and my orgasm was prolonged for a far greater time than any I had experienced previously.
Eventually my orgasm faded and I was a limp fuck doll being held in place by Mr Warren’s strong arms. I didn’t care anymore, I knew I would have to break up with my boyfriend if I was going to keep fucking Mr Warren, and I desperately wanted that. I realised he was whispering something in my ear but I missed the start of it.
“… slut. I’m going to cum inside you, blast your little womb with my sperm. I bet you’ll get pregnant, your belly will swell and those little titties will get fat with milk…”
“No, Mr Warren! I told you I’m not on the pill!”
“I knowwwwwww…. UGHHHHHHH!”
For the first time in my life I felt hot sperm blasting against my pussy walls, my cervix, completely coating my love tunnel with his seed. I could almost sense the little swimmers making a beeline for my fertile eggs and whimpered powerlessly. I was sure he was right, I would get pregnant from this, and then everybody would know what a little slut I was. The thought was strangely liberating and hot all at the same time.
Mr Warren’s thrusts slowed as I felt his jets of cum decrease in power and volume. Soon he was still and we stayed where we were, panting against each other in the afterglow. Eventually he released me and I raised myself up and off his cock, squeezing my pussy as tight as I could in an effort to keep his cum inside of me.
“Can I babysit for you next week too, Mr Warren?”
“I think that can be arranged, Sara.”
###
Breeding with the Reluctant Babysitter 2
Sara was a year above me in school, and we weren’t friends. If our school had cheerleaders she probably would have been one but I was always more of the artistic persuasion, part of the drama club, an aspiring actress. I remembered the scandal when she dropped out of school right at the end of the previous year. Rumour had it that she’d gotten pregnant, and her few public appearances afterwards proved those rumours true.
Given all that, I was certainly surprised to receive a phone call from her near the end of my own last year of school.
“Hello, Breanna?” the voice asked.
“Yes… who is this?”
“It’s Sara, Sara Mounce, from school. Remember me?”
“Oh, uh, yeah. Hi Sara, how are you?”
“I’m good thanks. Busy with the little one, but good.”
“Great. Anyway, to what do I owe the pleasure, Sara, this is a bit out of the blue?”
“I’ve got a job offer for you.”
“I’ve got a job.”
“I know, you’re a babysitter.”
“How did you know that?”
“Are you kidding me? You were my big babysitting competition last year before… well, you know. Some people would only contact me when you were all booked up.”
I was slightly flattered by the confidence my regulars showed in me and smiled to myself. “I am still keeping pretty busy with all that, not sure if I can take on any more.”
“I think you’ll want this one, Breanna. I had my own regulars you know, some really good ones, but I’m just too busy with my own kid now.”
“What’s so good about this one?”
“They pay pretty well for a start, the job this weekend is only a few hours and it will be $100.”
“Wow, that is good.”
“Yep, but there’s a couple extra perks… for the right babysitter.”
“What do you mean?”
“Well, they’re pretty loaded and, um, keep this to yourself, but I found where they keep a box of cash. They never notice if you take a little bit.”
“You steal from them?”
“Don’t get on your high horse, Breanna, when I took over babysitting for the O’Malley’s they told me you stole from them. Besides, I know you need the money, I’m not judging you.”
I was caught in a major conflict of emotions, embarrassment about being caught out on my false indignation, angry about Sara’s comment on my near-poverty-line home life, but also an undercurrent of interest about this job that sounded too good to be true.
“OK, sorry, just reacted that way out of… well you know.”
“No problem. There’s one other thing you can do to make this gig a bit more lucrative. If you’re interested that is?”
“Yeah, I’m interested.”
“Well, this might sound a little strange but hear me out, OK?”
“OK…”
“Well, you see, Mrs. Warren is a bit of a cold fish, doesn’t really give Mr. Warren a lot of attention from what I can gather. He likes to have a bit of, you know, eye candy around the place.”
“If you’re suggesting what I think you’re suggesting, there’s no way! I’m a babysitter, not a whore!”
“No, no! It’s nothing like that! Mr. Warren isn’t like that at all! He’d never lay a hand on you, but if you dress up nicely, like in a little schoolgirl outfit and just play up the little sexpot angle, you’ll find a healthy tip along with that $100 at the end of the night.”
“I don’t know about this… what if he gets the wrong idea?”
“Then you tell him no and he’ll listen, he’s not a psycho or anything, I’ve been babysitting for the Warrens for years.”
“Speaking of Warrens in plural, what does Mrs. Warren say when you arrive at the doorstep looking like a call girl?”
“Well, you won’t need to worry about that this time, she’s away. After you get your fat tip you can think of a way to get around that little obstacle if you want to do more babysitting for them. I know you can do this, Breanna, you were awesome as Juliet in Romeo and Juliet, just think of it like an acting job.”
“You’re sure he won’t try anything?”
“Positive.”
*****
I did everything just like Sara said, how could things have gone so disastrously wrong? I’d arrived at the Warren residence right on time in my shortest little tartan skirt and button-up white top. I even had my hair in pigtails, I wanted that tip!
Everything had been going so well, Mr. Warren’s eyes had nearly popped out of their sockets when he opened the door and saw me. He couldn’t help himself but scan me from toe to head, lingering at the hem of my short skirt. I’m a petite girl, so his eyes didn’t have too far to roam and by the time they reached my eyes I was twirling a finger around one of my pigtails, really playing it up. When he offered his hand in introduction I actually even gave him a hug, making sure my little breasts pressed into him. Sara had assured me that he just liked a bit of attention and wouldn’t get any funny ideas.
The Warren kids were well behaved and after putting them to bed I didn’t hear a peep out of them. I went to the drawer in the Warrens’ bedroom that Sara had told me about and lifted a couple hundred in twenties. Like I said, things were going great.
That all changed as soon as Mr. Warren returned from wherever it was he had been that night. I was ready to go but he said he just needed to check something in his room. I couldn’t help but be nervous, waiting for him to come back downstairs. What if he noticed the missing cash? I gulped and my heart began to beat faster.
“Breanna, could you come up here. Right now.”
If I could have seen myself in a mirror at that point, I’m sure I would have been as white as a ghost. His voice was quiet, so as to not wake his kids, but laced with a stern edge that carried it all the way down the stairs to my terrified ears. I had an extremely brief debate with myself as to whether I should go upstairs or run. The debate didn’t last long, if he had noticed the money then he knew all my contact details anyway, if he hadn’t then he’d certainly thing something was odd when his babysitter ran away.
I walked up the stairs towards his room feeling like I had a ball and chain around each ankle, I could almost hear the metal clanking. I peered into the softly-lit space and felt a momentary surge of hope, the drawer with the box of money wasn’t open, he was looking at something on a tablet PC with a completely unreadable expression on his face.
“Have a look at this, Breanna,” he said.
Mr. Warren passed me the tablet PC, on which a video of some kind was playing. I thought that was an odd time to be showing me whatever latest funny video clip was on the internet but my heart almost stopped when I saw it was a video of the very room I was standing in. Shortly after I registered that fact, I saw myself enter from the left side of the screen and perform the theft I had done earlier that evening.
I looked back up at Mr. Warren with tears beginning to run down my cheeks, leaving blackish-grey trails of my eye-liner, which had all been part of my sexy schoolgirl costume.
“Please Mr…” I began but he held up his hand.
“Stop right there, Breanna. There’s no way I can just let this slide. The only question is are you going to come peacefully to the police station or do I have to make a citizen’s arrest and restrain you? Such a shame, how you’ve thrown your entire future away.”
I literally dropped to my knees in front of him, carefully putting the tablet PC on the ground before grasping at his hands.
“Please, Mr. Warren, I’m sorry! I’ll give you the money back!”
“Of course I’ll get my money back, after the police have taken it from you.”
“No, please! I’ll do anything! I want to go to acting school, they won’t give me my scholarship if I have a criminal record!”
“Such a shame,” Mr. Warren repeated himself but seemed to be pondering something as he looked down at me.
I’d seen a similar look on my boyfriend, Matt’s, face the first time I let him see my breasts. There’s an unmistakable look of hunger that goes with lust and I knew I still had a bargaining chip. Two actually, and though small they were firm and full of the perkiness of youth.
“I’ll… I’ll let you see my boobs.”
One of Mr. Warren’s eyebrows raised a little as he glanced down to my chest.
“Oh?” he asked.
“Yes! Right now! No touching, though.”
“Let’s see them.”
I began to slowly unbutton my shirt, partly because I thought he would find it sexier but mostly because I was nervous as hell and my hands were shaking. My boyfriend Matt and I were both in the drama club and I’d lost my virginity to him the very night we first played Romeo and Juliet to a packed crowd in the school hall. It was magical, he was my one true love and the only boy who had ever seen me naked. I couldn’t believe I was about to show Mr. Warren what I had planned on saving for Matt forever, but if I didn’t then Matt might go to acting school without me and find somebody else!
The last button came undone under my fingers and my thin white shirt hung loose, exposing my taut navel and the strap of my bra between the two small cups. I looked up at him from my position on my knees, hoping against hope that he would just tell me to stop and that he would forgive me, but there was no forgiveness on his face, only more of that hunger. To add to my stress, my head was right in front of his crotch and there was no missing the fact that there was a swelling occurring in those pants.
The thought that a hardening cock was bare inches from my mouth startled me by how much it turned me on. When the idea when through my mind it was like a gentle jolt of electricity hit me between the legs, momentarily distracting me from my fear and nervousness. The sensation passed quickly, as jolts of electricity are wont to do, and in its wake I felt the beginnings of increased dampness in my depths. I squeezed my eyes shut, which forced two more tears out to run down the eye-liner trail, and offered a silent apology to Matt as I shrugged my shirt off and felt it land on my calves.
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