Blackmailed Into Servitude Ch. 05-07

Author's Note:

If you don't like blackmail/sexploitation stories where young [18-year-old] girls are coerced into having sex with an older man please don't continue reading.

Per usual, I'll be doing weekly releases, so please check out either my bio or the comments for updates! With that said, enjoy the read!

Chapter 5 :

The Price For My Freedom

Olivia 'Liv' Hartman | 18

Friday, September 30 ^th

Keeping my eyes shut and pretending that I was alone in my room the entire time I was masturbating for Scott was the only way to get myself wet. Doing that is the only reason I was able to bring myself somewhat close to climaxing. But now that I'm once again seeing this creepazoid staring hungrily at me from across the couch, the toe-curling, body-buzzing pleasure that had overtaken me seconds ago has instantly turned back into nervousness, leaving me feeling too uncomfortable to even wanna pull this toy out of me.

So, I look down before spreading my legs, and then, once my thighs are no longer clamped around my hand, I slowly pull the dildo out of my coochie. And despite how uncomfortable this situation has me, my body trembles in pleasure from the pleasant sensation of having the toy's flesh shifting along its rubber core as it glides out of my tight passage.

Unsure of where else to put this glistening dildo, I place it on top of my shirt that's bunched up on the middle cushion against the backrest. As soon as I begin crawling toward Scott, he scoots back to the arm rest and then stretches his legs out across the couch, giving me a clear view of the boner that's pitching a giant tent in the crotch of his pants. Instead of urgently undoing his jeans like I expect, he just sits there in an upright position and stares expectantly at me, smirking.

Of course this asshole wants me to undress him too, I think, once again mustering my best naughty smile and 'fuck-me-eyes' while reaching for his belt.

Since I want this to be over as soon as possible, I feverishly undo his buckle and then his pants button. Right after I unzip him, he lifts his pelvis and then I pull his jeans and his boxers down in one tug, allowing his surprisingly large erection to spring up and wag back and forth before me.

My eyes go wide. Geez... His dick is, like, two-inches longer than the friggin' dildo, I think, glancing from his penis to the sex toy beside me as I pull his bottoms past his ankles. He's a little girthier too... Might be the thickest cock I've ever seen in person... I'd be impressed if it wasn't attached to him of all people.

The moment I drop his pants onto the floor, Scott swings his legs back over the edge and then scoots back to the backrest. Now I reluctantly meet his gaze and begin walking toward him on my knees. By the time I reach him, my body is shaking, and my breathing is all ragged and uneven. As I swing my leg over his lap and come face-to-face with him, the anxiousness that overtakes me is so bad that it feels like I'm about to blackout.

"Hey," Scott whispers calmly, staring deep into my eyes I palm his shoulder, "just close your eyes, take a few deep breaths, and pretend I'm just a dildo suction-cupped to the floor, okay?" A warm smile follows.

I force a smile as I clamp my eyes shut. After inhaling slowly, I exhale even slower while reaching beneath me and holding his warm, twitching erection in place at the base. Another deep breath follows and, as I let the second breath out, I slowly lower my crotch toward his length.

"Mm," I whimper in rebellion the moment his warm crown presses against my vagina, my body shuddering violently in response to having part of him touch me there. It only takes one try to line him up with my tight entrance, and then I lower myself further to wedge his tip into me. "Ah-ahhh," I moan quietly from the unwanted pleasure of his penis's wide head finally stretching its way through my slick little hole, my body quaking even harder than before.

"ARRGH," Scott groans along with me. "Oh... Fuuh-k..." His body spasming against me as my vagina slowly swallows inch after inch of his length. "Can I—GRUHH—can I touch your waist?" His words come out strained.

"Yes," I respond in an equally strained tone as my stretching vaginal walls flutter from the sensation of having a bare cock impale me for the first time. As his large hands cup my hips, his erection reaches the end of the line, stopping only because his cockhead has just mashed against my cervix. "Ah-Ahh... Ah..." I groan quietly. It doesn't hurt so much as being touched that deep for the first time feels uncomfortable.

With both my hands gripping the headrest behind him, I rise from Scott's lap just a bit—until his crown is only just barely touching the tender flesh at the end of my cavity—and then I hold completely still, waiting for my pussy to accommodate to being penetrated by something this long and girthy for the first time. Not only have I never had a dick this deep in me, but I've also never felt this full and stretched out by any of my two ex-boyfriends in high school, the guy I hooked up with at the beginning of the semester, or the RealCock 2 dildo I pleasured myself with a bit ago.

A few seconds later, I finally muster the will to rise slowly—until maybe three-fourths of his length has left me—and then I come back down just as gradually, stopping right when his crown kisses my cervix. Despite having just toyed myself with the RealCock 2, having a real bare dick—a warm dick—gliding in and out of me for the first time feels incredibly different than condom sex. Better. I rise once more and, as I re-impale myself on his now thoroughly lubricated rod, I can't help but think that I'd enjoy this sensation if I was riding someone other than Scott Bonham.

Once I get the rhythm down a few bounces later, I ride him at a more moderate pace while also gyrating my hips, our flesh clapping each time I slam down onto him. I'm fucking him the way I used to ride my exes not because I'm enjoying it but because I want to do whatever it takes to make Scott blow his load as quickly as possible so this nightmare can finally end. Well, end for today, anyway.

"Oh... Urrrgh..." he growls in response, his hands gripping my hips a bit harder. "Yeah... Just like that, Liv."

"Ah... Ah-ahhhh..." I moan quietly as more unwanted pleasure buzzes through me, my cavity sporadically clenching around his too-girthy appendage.

Seconds later, his body tenses against mine, and then his left hand moves from my waist to my upper back, pressing me tighter against him. "GAH!" He spastically bores up into me with a jarring thrust, slamming his cock into the end of my cavity so hard that I wince. That's when his core begins spasming violently against me like someone is shocking him with a high-voltage cattle prod. "OHH-RAAH!" His cock throbs inside my fluttering canal. "GRAHHH!" As that bestial roar escapes him, I feel the never-before-experienced sensation of liquid heat spraying my cervix. "AH-Ha-ah-Ha-uhhhhhh-urrgh..."

Eww, I think, shaking my head as he humps up into me again with another short, spastic thrust while he also pulls me down harder against his lap. When I feel another spurt of semen blast right against the end of my cavity, I squeeze my eyes shut harder than they have been during this entire transactional sex act. Just... eww... I can't believe this asshole is the first guy to ever finish inside of me.

For maybe ten grueling seconds, Scott holds me against him, and he doesn't loosen his embrace until his erection stops throbbing inside of my vagina—until his body stops spasming against mine. "Ho-lee fuugh-kuhh," he sighs out breathlessly like he was the one doing all the work. "That was probably the best sex I've ever had." His arm un-snakes from behind my back. "Thank you, Olivia."

"You're welcome," I mutter through gritted teeth in the most insincere tone possible while I lean away from him.

Instead of letting me dismount so I can pull his softening dick out of me, he palms my hips with a firm grip and holds me in place while staring deep into my eyes. "It wasn't that bad for you, was it? Because it kinda seemed like you were enjoying yourself a little bit."

I shake my head.

"You shaking your head no to it not being that bad or no to somewhat enjoying it?"

"No, it wasn't that bad," I say flatly.

He scans me with the intensity of a cop interrogating a murder suspect. "You're not lying to me, are you, Olivia?"

"No," I say, shaking my head again.

"Good. And was riding me at least a little pleasurable for you? Or was you moaning while your pussy contracted around my cock just you putting on a show?"

After a moment of consideration, I nod. "Yeah... I guess there was, like, a second or two where I forgot who I was fucking and things were somewhat... enjoyable."

He nods. "Excellent. Don't worry, I'll get you to start enjoying every second of our time together eventually. But, for now..." Scott's left hand moves to the small of my back as his right slides up to my neck, and then he rolls onto his left hip and lays me backside down onto the couch like a sleeping child he's putting to bed—he does all of that without letting his cock skip out of me. "Lay back against the armrest and spread your legs for me, sweetheart," he growls while finally pulling his flaccid and yet still lengthy member out ever so slowly, staring between my legs with wild eyes and a grin as he does. "Wow. I can't believe nothing dripped out... Thirsty cooch you got there, Liv."

Like the obedient little sex servant that I am, I do as I'm told without delay, scooting back and assuming the position I was in before he made me touch myself. Meanwhile, Scott grabs his pants and mine from the floor.

"Okay," he says, pulling his phone out of his pocket and holding it up like he's recording me again, "I want you to take your middle finger and dip it all the way into your pussy so you can feel how much cum I filled you up with."

I look down and reach between my legs. "Uhh," I whimper quietly as my finger glides into my tight, jizz-slickened passage.

Never in my life has my coochie been this slippery before.

"Good girl," he growls once my digit is all the way in, the tip of my finger now marinating in a reservoir of thick goo. "Go on and pump it in and out a few times."

I comply without hesitation. Schlick-schlick-schlick—my coochie squelches with each withdrawal and gushes noisily with each penetration of my finger. "Ah-mm..." I groan, more out of disgust than pleasure.

"Good girl..." he whispers. "Now, curl your finger forward while pulling it out, and then take a good look at what I filled you up with."

I do as I'm told, and then I stare in awe and horror at the pearl-white slime coating my finger from its tip to just past my second knuckle, trying not to let my revulsion show on my face. Gross... So gross.

"Good, good... Now suck your finger clean for me," he demands.

Slowly, I bring my trembling hand to my mouth, and then my tongue spasms in response to the taste of jizz on my finger as I wrap my lips around it. Now I pull my hand away while sucking off the coating of briny, bitterness, doing my best not to let the disgust show on my face. Despite my best efforts, I wince, but I quicky try to mask it with a quivering smile as my finger leaves my mouth with a smack.

"Good girl," the grinning man rasps while lowering his smartphone. "You're really nailing this whole obedience thing now..." He tosses my panties onto my belly, drops my shorts between my legs, and then gestures for me to put them on.

I swing my legs over the couch and scramble to slip my feet through the holes of my underwear. "Not like I got a choice," I mutter.

"You always have a choice, Olivia." He looks from me to his phone and then starts thumbing away at the screen. "This can end whenever you want it to. I'm not forcing you to do anything."

I rise from the couch while pulling up my panties. "Yeah, except, if I want out early, you go to the cops with the security footage, right?"

"Of course... That's the deal we made," he says flatly without looking up at me, still texting or whatever he's doing.

"Well," I groan while putting on my shirt, "then I guess I have no choice but to see this through to the end. Because there's no way in hell that I'm breaking our deal after what just happened."

"That's what I was hoping you'd say," Scott says with a grin, glancing up at me for a second before looking back down at his phone. "Because I'd hate to turn you in after having you fuck me. That'd honestly make it real hard to sleep at night." A few moments of silence pass, and then he finally looks up at me just as I'm pulling up my shorts. "Alright..." He grabs his boxers and then slips them over his feet. "I just ordered you an Uber. Should be here in five minutes." Just like I did, Scott rises from the couch while pulling up his underwear, his long, flaccid penis swinging like a pendulum as he does.

"Oh... Thanks," I mutter, looking down at my hand. "Can I use your bathroom?"

"Sure," he groans while pulling up his jeans. "It's right across the hall."

As soon as I get my sneakers on, I power walk to the door.

"Oh, and Olivia?" Scott blurts out right when I grab the knob.

I glance over my shoulder at him. "Yeah?"

"If you're gonna tinkle, don't go fingering out my jizz while you're on the toilet," he orders sternly. "I'd like it all to leak out on its own throughout the evening. That way, every time you feel your panties get wet and sticky while you're walking or sitting around, you'll think of me."

"Uh... As you wish," I say sarcastically, opening the door.

"Hold up," he commands, making me stop dead in my tracks. "I'm serious... In fact, I may or may not text you randomly tonight asking you to send me a video of you pulling down your sticky undies and fingering out whatever's left as confirmation that you obeyed my wishes like a good little girl. Or maybe I'll swing by campus tonight and make you strip in my Jeep so I can confirm for myself. And if I find out you've disobeyed me, well... the consequences will be dire."

My face scrunches up in disgust. "You're joking..." I scan his deadpan face. "You're joking, right?"

"Maybe I am, maybe I'm not... Just in case, unless you have to use the toilet, don't remove those panties until I see you tomorrow. Actually... don't bother showering until I tell you to. We'll consider that your punishment for being a dirty little criminal." A fiendish smirk creeps across his face, and then he winks. "You can go ahead and use the bathroom now, Olivia."

"Ugh," I groan under my breath, rolling my eyes as I storm out of the office.

Contrary to what I expected, the windowless bathroom that I walk into is clean and smells fresh, and the toilet that I peek at through the partially opened stall door is spotless. Still, because I'm a bit of a germaphobe when it comes to bathrooms, I lay tissue down on the seat before sitting on the toilet. And because I'm genuinely concerned that Scott will make me verify that I didn't purge myself of his load when I return to his office, I don't push too hard while I pee. Thankfully, it looks like only a tiny drop of baby batter leaked out when I check the water below.

This is unbelievable, I think as I flush the toilet. I cannot believe that I'm being forced to obey such absurd demands.

The moment I leave the stall, I look down at the sink and I don't glance up at the mirror once while washing my hands. After what I did in the office with that man, I'm too disgusted with myself to see my reflection. I guarantee that if I look myself in the eye right now, I'll breakdown in tears and become an inconsolable mess.

"Uber is two minutes out," Scott says from behind his desk the instant I step foot back into the office.

"Okay," I mutter, not looking him in the eyes. "Can I wait outside?"

"Sure. If you wanna." He opens his top drawer, grabs something, and then holds it out to me. "Here's your phone. And, as promised, here's sixty-bucks for a morning-after pill and a drink to wash it down with."

"Oh. Thank you," I say flatly, taking my iPhone and the three twenty-dollar bills from him.

Now he holds out his phone to me. "Before you leave, go on ahead and put your number in my phone for me, please. I'd rather you give it to me than me asking my P.I. for it."

Nodding, I take the device from him. It only takes a few seconds to put input my info. "Here," I say flatly, setting his phone on the desk.

"Thanks." He pulls it across the table then hits call. Two seconds later, my phone starts buzzing in my pocket. "Now you've got my number." He taps End Call and the buzzing stops. "I know you'll be busy with classes and parties and sorority stuff during the duration of our arrangement, but try not to be too unresponsive when I text you, alright?"

I nod. "Don't worry, I'm not stupid enough to ghost the guy who's blackmailing me."

"Perfect. Because I'd hate to have to punish you for leaving me on unread for too long... Also, this probably goes without saying, but... whenever I ask you to come see me, or if drive to FSU and ask you to meet me somewhere, I expect you to show up no matter how late or early it is. Is that understood?"

"Mm-hm. Understood," I say through gritted teeth and a fake smile.

"Good girl. On that note. What time do you normally wake up on weekends?"

I shrug. "Depends how hungover I am... I'm usually up by nine though... Why?"

"Just asking in case I wanna schedule a morning get-together... Also, for future reference, how do you like your coffee?"

"Uh... Iced. Two sugars, two creams. That or an iced latte with the same amount of sugar."

"Cool. And, final question... What're you doing tomorrow night?"

I shrug again. "Probably going to a party."

"ERRR," he bleats, imitating the sound a buzzer makes. "Wrong answer. You and I are having dinner tomorrow night at 8:30 sharp."

"Yippee..." I say in the flattest, most sarcastic tone of the day.

"Ah, c'mon, Liv," he says, waving me off. "It won't be that bad! Getting to chat and know each other over a delicious meal and maybe some wine or your alcoholic beverage of choice—if you want to drink—might help make our arrangement a little easier for you to get through. At least, I'm hoping this becomes easier for you once you get to know me a bit better."

I sigh. "I guess we'll see."

"Guess we shall..." His phone buzzes on the desk before him, prompting him to look down. "You're Uber is out front. Dark Blue Toyota Rav4," he says, turning his phone to me so I can confirm for myself that the vehicle outside is an actual Uber driver. "I locked the front door for our meeting, so leave through the rear."

"Oh... alright," I say as I start toward the door.

"Text me when you get back to your dorm, okay?"

"Kay."

"See you tomorrow, Olivia."

"Yup."

The moment I step into the hallway, I start power walking to the gray door to my left. And the instant I burst through the exit and emerge into the warm, late afternoon air, my legs pick up speed on their own accord as my eyes begin to burn. Then, right when I round the corner of the building and set my sights on the parking lot, something sticky and wet in the crotch of my panties smears across my folds.