Blackmailed Into Servitude Ch. 01-04

I shake my head and stare at the list of activities. "So, if I sign this—if I agree to this option, you get to take me and touch me whenever you want every day for five weeks—"

"Hold on," he interrupts, "Like I said before, I'm gonna let you initiate everything at first until you're comfortable with us being intimate. I want this to be one-hundred-percent consensual, and I don't want this to feel like assault at any point, which is why I'm not gonna just bend you over my desk and take you immediately after you sign this. For as long as it takes, whenever I summon you here or to my home to fulfill your contractual obligations, I'll just sit there and let you service me until you tell me it's okay for me to self-serve myself using your body. That's a promise."

That gives me some sense of comfort, but I won't let him know that. "How noble of you..." I sass, glancing back at the document. My gaze wanders to the part about how I must make my body available to him every day. "So, what happens during the days I'm on my period?"

His mouth twists to the side and he snaps his fingers. "You know what, I didn't even think of that..." He pulls out another copy of the contract from the folder before him, clicks his pen, and starts writing. "I guess we'd do everything else until your time of the month ends, and then we could make up for those lost days of sexlessness in November."

"You said five weeks, and now you're adding more days?"

"Sorry, but you didn't agree to anything yet, nor was the deal inked yet. So... I'll just add, what? Five more days then?"

I clench my jaw so hard that my teeth hurt and my ears ring. "Whatever."

"Cool... That makes the end date—" He glances at his calendar. "Friday, November 11^th... But, since I'll be missing out on time with you while you're in class, I'm just gonna go on ahead and make the end date November 13^th. That way, I can get another full weekend," he mumbles, scribbling in the new date. "And before you fret, that's non-negotiable."

I huff, shaking my head while I continue examining the updated copy that he just slid over to me. After glancing at the new contract end date, I look at Section III. "Some of these allowed activities are a little outrageous..." I groan. "Like, you don't have to wear a condom at all, and you get to finish in me even if I don't want you to?" I glare at him. "I don't have unprotected sex. Ever. And because I don't, I'm not on birth control."

"Well, you're gonna need to get on it now. Also, there's a reason I put that bit about giving ya money for the morning-after pill until you are."

I shake my head. "Oh," I say pointing at the last allowed activity, "and you get to record what we do?"

Scott bobbles his head. "Yup. And as per the confidentiality section, those recordings will be for my eyes only, I promise."

"So... Would I have to agree to all of the activities you initialed next to?"

"Yup. Every. Single. One. Non-negotiable."

"Unbelievable..."

He shrugs. "Hey, if you don't like it, you don't have to sign it, Olivia. Like I said before, you're not being forced. You can walk whenever you want."

I huff and just stare at the document, skimming it over and over line by line until I zone out and enter an unblinking trance. It's this or jail... Giving my body to this creep every day for six weeks will suck, but jail would suck worse... And at least he promised that he'll let me initiate everything and let me be 'in control' until I'm ready to let him dominate me... because there's no way I could handle getting held down and fucked like a sex doll for just over six weeks.

My heart throttles and dizzying anxiousness overtakes me as my eyes flood with tears.

This is the price for my freedom... And 44 days of being his personal fuck doll is a much smaller price to pay than having my life ruined over some stupid sorority hazing challenge.

Without looking up at Scott, I hold my hand out to him. "Give me a pen please," I mutter through clenched teeth.

"Yeah?" he says excitedly, and I can tell by the sound of his voice that grinning. "You sure?"

I sniffle. "Just give me a pen," I snap.

"Here you go," he says, placing the blue clicky pen on top of the document before me. "And when you're done that, please also sign this NDA. In a nutshell, it says you won't discuss anything about what we talked about here today and that you'll never speak of me hiring a P.I. to bring you in."

"Whatever..." Without delay, I begin initialing beside all the allowed activities that he wrote his initials next to. After that, I initial and date the contraception use agreement section. When I get to the signature line, wipe the tears forming in the corner of my eyes and then glance up at him. "Our verbal agreement... What is it?"

"If you uphold your end of this contract until November 13^th, you're 100% absolved for the felony you committed. You have my word that I will never submit the surveillance footage to the authorities and that I'll delete all recordings of you robbing my store last week. And I swear that I won't blackmail you after that." He offers his hand to me. "Deal?"

The last thing I want to do is touch him but, considering his dick will probably be inside of me within the next few minutes, I put the pen down and reluctantly shake his large hand. "Deal," I say just above a whisper. Once he lets go, I pick up the pen and stare at the blank signature line for a good ten seconds. Then, after letting out a long huff, I sign my name and then write the date beside it. After reading the NDA, I do the same. "Here." With my head turned to the right so I don't have to look at him, I push the documents across the desk.

"See, I knew you'd make the smart move!" he says cheerily. In the silence that follows, all I hear is the pen scraping across the desk beneath the page as he signs his name. "Now that that's done..." When his words trail off, I side-eye him as he's grabbing the RealCock 2 dildo from his desk. "Here."

I squint at the brown-skinned phallus he's holding out to me, my eyes scanning the toy's flesh that has realistic veins, texture, and detail down to the wrinkles on its ball sac. If some guy texted me a picture of this thing sticking out of their boxers, I'd without a doubt think it was a real, flesh and blood penis. "Um... What's this for? Is this as a gift for signing the contract?"

Scott snickers and grins menacingly. "Uh... Yes and no... As a way to... break the ice and ease you into things, I want you to undress and show me how you'd play with this toy."

My eyes go wide. "Seriously?"

"Yup..." He points at the contract, his finger tapping next to the fourth to last allowed activity. "You agreed to obedience play, right? Well, me telling you what I want and you executing my request is what that looks like... So take this, strip, and get yourself off like I'm not even here." He wags the sex toy in front of my face, making it flop side to side like an excited dog's tail.

I huff. "Okay..." I curl my fingers around the dong that makes my fair- skin look even lighter by comparison.

As I pull the 6.5-inch-long sex toy from his grip, this dildo's silicone skin slides along the squishy but firm rubber core beneath it the way a real penis's skin would move around the erect tissue below. That's not the only thing that makes this thing feel so realistic. When I was here last week messing around with the display model, I discovered that this thing's balls even float around the silicone scrotum just like real testes do.

Last week, I couldn't help but fantasize about pleasuring myself with one of these. But now? Now that this creep is forcing me to do so in front of him, it's the last thing in the world I want to do.

Scott rises from his seat. "The longer you sit there trying to psyche yourself up, the longer you're going to be here, Olivia," he says while walking by me. "C'mon. I've got an appointment around five o'clock, so lose them clothes and join me on the couch."

My body trembles so badly that the dildo starts flopping around in my grip. Fuck... Fuck me... I can't believe I'm about to masturbate in front of this guy, I think as I rise from my chair.

You can do this, Liv. Sigma Lambda Tau basically prepared you for this, I remind myself, referencing the Sybian interrogation challenge we did the day before the heist.

If you could get off in front of a room full of girls and a bunch of random frat boys, you can do this, Liv...

Chapter 4 :

Show Me How You'd Play With This Toy

Scott Bonham | 32

Friday, September 30 ^th

The instant I stroll past Olivia, I grin harder than I ever have in my life—I grin so hard that my cheeks and jaw hurt. I can't believe this whole blackmail plan worked out perfectly, I think while walking across my office.

Along the way, I glance at the bookshelf on my left to make sure the 4K camera I setup earlier is still recording. Since the red light is still blinking, I move her backpack from the couch to the floor, and then, with my gaze fixated on the teary-eyed girl who's still standing by my desk, I flop down onto the cushion closest to the door.

Then again, how could it have not worked out? Of course she'd pick being my sexual servant for nearly six weeks over jail and expulsion from college, especially after I strategically scared her with the extreme gloryhole sentence that I coerced Taylor—A.K.A. Blondie—into serving out last weekend.

"Ah, c'mon, Olivia," I say, flashing her a sympathetic smile. "I hate that you're all distraught and petrified over there... I mean, I completely understand that this situation isn't easy for you, and I know it sucks having to perform intimate activities for some stranger, but I'm gonna need you to cheer up and get in character for me, okay? It needs to feel like you're enjoying putting on a show for me. Otherwise, the deal is off." That command comes out sterner than intended.

She nods subtly, sniffling and wiping a lone tear from her cheek.

"That needs to be true for everything we do moving forward too," I continue. "Every second of our intimate time from this moment onward has gotta feel like you want it as bad as I do, you understand?"

She nods again. "I understand."

"Good girl! I'll tell ya what... I've gotta send a couple of texts before I start recording, so you have about a minute to muster up a naughty smile and your best fuck-me-eyes before you come over here, alright?"

Her big blue eyes go wide. "Do you have to record this? Like, it's already gonna be hard enough using this thing in front of you without a camera being pointed at me," she whimpers in a bit of a southern drawl.

"Yes, I absolutely do," I say, glancing down at my phone and tapping on the message icon. "I mean, how can I not capture such a glorious experience? Besides, there are security cameras in here, remember? So it's not like it wouldn't be filmed anyway." I look back up at her with a smirk.

She bobbles her head like she just had an 'Oh yeah' moment. A beat later, she closes her eyes and sits on the edge of my desk.

As my attention returns to my phone, all I hear is Olivia inhaling deeply only to exhale slowly a moment later. That's right, do your breathwork to calm yourself down, gorgeous, I think while thumbing my message to Private Investigator Jonathan Brady.

My text to him reads: Hey, Jon. Olivia and I have finished our negotiations. It's looking like she'll be out of here by 4:00, so you're all clear to bring in Faith at 5:00.

After tapping send, I open my conversation with my buddy Marty Bateman and get to texting.

Me to Marty: Yo, bro! It's looking like a new girl will be in the booth around 6:00. Get here like 10 min early this time so you can get first dibs!

Well, that's not entirely true. Unlike with Taylor, I'm gonna be the first one to fuck Faith Hanson through the gloryhole. Marty will technically be the first customer to unload in her though.

Out of all my regulars who race here every time they hear a girl is gonna be working the gloryholes, he's the only one who gets a personal text instructing him to arrive early. Because we've basically become brothers since he began frequenting my shop. As for everyone else who I messaged earlier this week to get tested in preparation for Faith Hanson's arrival today, they'll either receive a group text or an email blast about her 6:00 p.m. start time once her sorority sister Olivia has finished satisfying my needs.

Right after hitting send, I open the camera app and then look across the room to find Olivia sitting on the edge of my desk with tear-free eyes, slightly raised brows, and her mouth partially agape—an expression that's less miserable and more pouty in the sexy French model about to take a picture sort of way. And the second she catches me looking, her expression softens even more into something close to a smile.

A smirk creeps across my face. "That's more like it, Liv," I say as I hit record. "Come on over here, beautiful girl."

This time, my curly-headed sexual servant moves without hesitation, the silicone cock gripped in her hand wagging stiffly with each step. Instead of coming right up to me, she veers off toward the left side of the couch and stops, kicking off her sneakers before turning to face me. She doesn't sit though, she just uses her free hand to hold the opposite sleeve in place while pulling her arm and the hand holding the dildo through. Her waist-length curtain of brown hair rises off her body as she pulls her gray top over her head, and then I finally set my sights on her narrow waist and those perky, A-cup tits with tiny pink nipples.

The boner I've had since she walked into my office throbs in response. Holy hell... It's better than I imagined...

After dropping her shirt on the cushion beside me, she unbuttons her shorts, tucks her thumbs into the waistband, and then starts tugging them and her panties down with a little shimmy that's more innocent than it is erotic—she does all of that without once putting down the dildo. Unfortunately, her crazy long mane drapes down in front of her when she bends over to step out of her bottoms, blocking my view of the pussy reveal. Then, two or three torturous seconds later, she finally stands upright and whips her hair back as she kicks her shorts off to the side, giving me a clear view of her hairless vagina between that perfect thigh gap.

My dick throbs harder than last time. Fuck, she's perfect, I think as I zoom in on the pink inner lips dangling out from between her plump folds.

As she crawls onto the couch, I turn and sit back against the armrest, tracking her with my phone's camera without looking at the screen. I'm probably botching the shot, but this is too magnificent not to witness live. When Olivia finally leans back against the armrest, she brings her knees to her chest and then spreads her legs, prompting me to zoom in on the pink meat curtains protruding from between her bald folds and her tight little entrance that looks too small and tight to even fit my pinky.

My dick spasms over and over like I'm about to cream my jeans already. God... her pussy is literally the most beautiful thing I've ever seen, I think, licking my lips as I look up from my screen to truly take in the glorious sight. This is the best day of my life... Shit, part of me wants to tell her to just straddle me right now instead of toying herself because I need to be balls-deep in that immediately!

With her gaze trained between her legs, Olivia grips the RealCock 2 dildo by the base of the shaft, brings it down to her pussy, and then begins brushing the realistic cockhead up and down against her slit. After a few passes, she uses her other hand to spread her inner lips, pressing those large skin flaps against their respective folds like butterfly wings—like butterfly wings made of big pieces of chewed bubble gum. Now she presses the toy's cockhead against her tight entrance.

"Ahh," she moans quietly.

"Psst," I whisper as quietly as possible. When she looks up at me, I mime clit-rubbing over my crotch and then I make a 'come here' motion with my middle and ring fingers—my way of instructing her to make herself wet first by masturbating.

Olivia doesn't nod, she just looks back down while removing the dildo from between her legs, using her other hand to rub her clit immediately after. A moment later, she shuts her eyes and begins rubbing faster. Her chest heaves as her breathing quickens. Her body squirms ever so often. The hand holding the dildo against her belly squeezes the phallus harder than before. The longer she goes at it, the more ragged and labored her breaths become, and the more her petite body writhes in sweet agony.

"Ah... Ah-mm," she moans quietly a minute into it, her toes curling in her gray socks.

A few rubs later, she stops and then slides her hand lower, her middle finger dragging down her slit until she finally curls it into her entrance. Her other fingers splay out as she slowly inserts the middle digit into her depths.

"Ah..." she sighs out once her finger dips in as deep as it'll go.

A moment later, she retracts her digit at a faster pace than she pushed it in with, and it makes a deliciously wet, creamy noise.

Oh yeah, I think, watching the zoomed-in image of the wet finger leaving her. Fuck...

Olivia's eyes open momentarily as if she's checking how wet she is and, right after her eyelids clamp shut, she slips the finger back in. Schlick-schlick-schlick—that's the sticky, wet noise coming from her flesh pocket with each insertion and withdrawal of her digit. A dozen or so quick pumps later, she pulls out only to slip both her middle and ring fingers into her passage right after.

Schlick-schlick-schlick-schlick! Now that she's using two digits, Olivia's rapid fingering has her vadge making more sticky noises than before.

Barely thirty seconds later, things get even wetter sounding. Not too long after, she begins gushing so much that juices are dripping down into her palm and onto the couch cushion.

Good God... she's ready now, think, lightly tapping on the wall to get her attention.

When she finally opens her eyes, she glances up at me with this shy, sleepy, pleasure-drunk look, and then I point at the dildo.

Without missing a beat, she brings the sex toy between her legs and pushes it against her entrance until the thing's cockhead finally slips into her.

"Ah-mm," she moans while slowly impaling her tight passage with the not-too-girthy dong, her eyelids clamping shut once again. "Mm-HNG..." is the sound she makes when it finally bottoms out.

Just like her fingers did, the realist toy's skin comes out glistening with her juices when she starts withdrawing it, and it makes a wet sucking sound as it slides out. Right before the dildo's cockhead is about to slip out of her, she jams it back in much quicker this time. The sticky, creamy sound it makes going back in drives me absolutely mad.

In and out, in and out—her pussy schlicks with each somewhat moderately-paced pump. Much like when she began pleasuring herself, Olivia's breathing quickens, her body writhes restlessly, and quiet groans of pleasure rattle in her throat.