The Blackmailed Graduates Ch. 04

"Stacey, come her, honey," Ms. Wescott said gently.

Stacey took a deep breath in, stood up, and slowly walked over to Ms. Wescott with her head hung low. She looked like a death row inmate at the end of her sentence, walking to the execution room.

"Now step up here, and show Megan what you're made of," Ms. Wescott told Stacey.

"Please don't make me do this," Stacey again pleaded with Ms. Wescott, tears welling up in her eyes and starting to dribble down her beautiful face.

"We've already talked about this. If you want to have a white wedding, this is the price you have to pay. If not, there's the door," Ms. Wescott said calmly with her arms crossed. "Just be sure to remove your strap-on before you leave, or else the neighbors might give you some strange looks," she added with a smirk and a light chuckle.

Stacey paused for a moment of silent contemplation. I knew exactly what was running through her mind: her future, and her family. She was thinking about what those closest to her would say about her indiscretions. She was thinking about her engagement to the guy of her dreams, and what he would do. Her entire way of life was in jeopardy, and she had to decide what she would be willing to to do protect it.

Stacey took a deep breath, and made her decision. I watched as she stepped on top of the kneeling bench, and proceeded to insert the sex toy strapped around her waist into Megan's waiting cunt.

Given the height of the bed, the kneeling bench, Stacey herself, and Megan's elevated hips, Stacey had to learn forward and spread her legs wide in order to get a low enough base in order to get the correct angle of entry needed; this position also caused Stacey's ass to stick out prominently, making her pussy more exposed and vulnerable.

Stacey started to slowly thrust in and out of Megan in a very awkward, amateurish fashion. We all knew, I'm sure Stacey included, that Megan may never reach an orgasm with the current low level of technique and skill being deployed.

Nevertheless, Ms. Wescott was standing by her side, looking upon the scene with happiness and approval written all over her face. "Good girl, Stacey!" she said encouragingly while softly caressing Stacey's back. Megan let out an occasional moan, probably as her own form of encouragement as well.

Ms. Mescott let this go on for some time before jumping up on the bed herself. She got on her knees beside Megan and Stacey, and placed her large, ruby red, 9" strap-on dildo between their mouths, just like she had done to Jessica and I several months earlier.

Seeing Stacey's reluctance to participate in this sick, sexual act, Ms. Wescott grabbed the back of her head and forced it down as she slowly and carefully thrusted it back and forth between the two girls. "Show Lilith some love, ladies. Your saliva helps to stimulate her, so make sure you get every inch," she said.

Once satisfied, Ms. Weacott slithered off the bed and silently moved directly behind Stacey.

I could see a worried look come across Stacey's face; and she had every reason to be alarmed. We all knew what was coming next, and considering that Stacey was now gradually slowing to a stop with Megan, I'm sure that she had a pretty good idea as well.

"Stacey, it's time for you and Lilith to become intimately acquainted," Ms. Wescott said, placing the head of her fake cock at the entrance of Stacey's wet pussy. My heart sank knowing that I could have prevented this, and that I didn't do enough.

Ms. Wescott then spent the next few minutes pushing her way inside of Stacey, inch-by-inch, while we all watched. She always took her time, making sure to not rush anything, and she always allowed her victims time to adjust. In that respect, Ms. Wescott was kind, even if it did serve to further her own, wicked goals.

While Ms. Wescott continued her work, Megan wrapped her arms tightly around Stacey and pulled her in for a long kiss. This action may have been to help distract Stacey from what was happening to her, it may have been to show Ms. Wescott her eagerness to help, or she may have just genuinely wanted to kiss Stacey. Whatever the reason, this act from her gave me pause, and I wondered to what extent Megan regretted or had any guilt for what she had done to this innocent girl.

"There we go! All in!" Ms. Wescott gleefully exclaimed as she leaned forward onto Stacey, sandwiching her on top of Megan, and causing Stacey's strap-on to further impale her former friend.

"I told Lilith that it was going going to be a tight fit, and that she'd have her work cut out for her... I was right!" Ms. Wescott said with a large smile on her face. "She always enjoys a challenge, though. And when I told her that you were a gorgeous, engaged teenager, she said that she could hardly wait to meet you," Ms. Wescott continued, speaking right next to Stacey's ear.

Ms. Wescott, who towered over the young girl below her, then started gradually pumping her hips up and down in extremely controlled motions, causing Stacey to grunt as the evil toy slid in and out of her wet, virgin cunt.

Megan, who was being pinned under the two women on top of her, and who was now at least partially subject to Ms. Wescott's strap-on pounding, started to let out a few authentic moans of pleasure as well.

Seeing Stacey getting pressed on top of Megan's perfect, robust tits while Ms. Wescott took her from behind was quite a hot sight to behold, which is something that I hate to admit. As much as I despised Ms. Wescott, and even Megan to an ever increasing degree, the show that they were putting on stirred inside of me a feeling that I've always tried to repress and put in check; however, with Jessica's fingers roaming between my legs, this was extremely difficult to do.

After quite some time had passed, Ms. Wescott straightened up, grabbed ahold of Stacey's hips, and said, "Stacey, I know that you may not want to completely give in to Lilith, which is only natural; in fact, it's to be expected. But I just want you to know that she can and will outlast you, and that she has a flawless track record." Ms. Wescott then continued to hump Stacey at a steady, rhythmic pace, making sure that her girthy sex toy reached the furthest depths of Stacey's tender womanhood with each thrust.

Despite being somebody who serves the Lord of Lies, and who revels in deception, Ms. Wescott was telling the absolute truth. Of course Lilith is an inanimate object that will stay semi-ridged no matter what happens, contrary to Ms. Wescott's delusions of it being some sort of demon; that much is true. But more importantly, the woman who wields the toy, Ms. Wescott, has an almost unnatural sexual stamina. When she gets to have free reign on a young woman, they always end up as a quivering pile of flesh, spent and exhausted from their multiple orgasms, while Ms. Wescott herself remains excited and energetic. She is a true master of her sinister craft.

Stacey must have taken Ms. Wescott's words to heart, because several minutes later, her grunts and whimpers started to turn into pleasurable moans. Her body language also changed, as she started moving her ass back-and-forth, meeting Lilith on each inward thrust, and retracting on each outward thrust, causing the pounding to intensify.

Ms. Wescott, of course, was elated to see Stacey finally starting to enjoy herself, and she looked down on Stacey with a smug, "What did I tell you?" smirk on her face.

Knowing that Stacey was close to climaxing, Ms. Wescott abruptly pulled out of her, and quickly replaced Lilith with two of her fingers, facing palm down. Stacey gasped, furrowed her brow, and looked back at Ms. Wescott, who at that point was already buried up to her first knuckles.

"Oh my God, Stacey! Your pussy is throbbing so hard! You've got a strong heart, young lady," Ms. Wescott said with exhilaration and wonderment. She then slowly withdrew her soaked fingers from Stacey's pink, gaping cunt, and slid them down to Stacey's swollen clit, where she made small, firm circles on it.

"You've got one of the prettiest pussies I've ever seen. I mean it," Ms. Wescott said, as if her compliment meant anything to Stacey.

Ms. Wescott then slid her fingers back into Stacey's cunt and finger banged her for several seconds, making Stacey squeal and squirm, before finally stopping to put Lilith back in.

With her sex toy now back inside of Stacey, Ms. Wescott placed both of her hands on Stacey's shoulders. Not giving her newest victim even a moment of rest, she then redoubled her efforts as she made long, hard thrusts, slapping against Stacey's ass with an audible noise each time.

Finally, and predictably, Stacey's first orgasm of the night arrived within a few short minutes. With her face turned towards Jessica and I, she grasped the bed sheets tightly in both hands, squinted her eyes, held her breath, and then let out a moan so intense that it left no doubt in anyone's mind as to what was happening to her.

Within just a split second of the start of Stacey's climax, Ms. Wescott again leaned forward on top of her, pinning her hard against Megan as she continued her merciless assault. Simultaneously, Ms. Wescott leaned her head to the side and took Stacey's right earlobe into her mouth; she bit, nibbled, and tugged on it without breaking rhythm for a even single moment with her strap-on. This attention on her ear caused Stacey to turn her head slightly towards Ms. Wescott, and seeing her opportunity to join in, Megan lifted her head and started kissing Stacey on her neck, and behind her other ear.

Ms. Wescott and Megan worked on Stacey for as long as it took for her orgasm to completely subside; which, given how hard they were going on the poor girl, was so long that it started to border on torture.

Everybody eventually came to rest in their current positions, laying together in a sweaty, panting heap, with both Megan and Stacey both still being fully penetrated by the women in front and behind them, respectively.

Stacey looked back up at Jessica and I with the most glazed over eyes that I'd ever seen. Again, I felt an overwhelming sense of sorrow at what a failure I had been to save her from this fate. Now, her innocence and virginity have both been taken from her in the most spectacular fashion, and I'm to blame for it.

"Stacey, I want you to have a happy marriage... I really do," Ms. Wescott said in a kind voice, still buried balls-deep in Stacey from behind. "But if your husband is never able to make you cum as hard as Lilith did just now, which is almost a certainty, I don't want you to hold it against him. Can you promise me that?"

Stacey was speechless, as was to be expected. Nevertheless, she nodded her head slightly, possibly not wanting any repercussions from ignoring a question.

"Oh, good! Thank you, Stacey," Ms. Wescott said. "I'd hate for her to be the cause of any marital strife. She's just doing what's in her nature," she continued as she straightened back up and slowly withdrew her dildo from Stacey's freshly defiled, pink, teenage pussy.

Ms. Wescott then reached over to her nightstand and pulled out a slender, smooth, purple vibrator. "Stacey, help me finish off Megan," she said, flopping on the bed next to them.

With Ms. Wescott pressing her vibrator to Megan's clit, and an exhausted Stacey continuing to make awkward, half-hearted thrusts with her strap-on, it didn't take long before Megan had her own orgasm. It was surreal, and disheartening, to see these two girls whom I had helped to entrap, now engaged in this sexual act with each other.

With Megan satisfied, Stacey pulled out of her and started to slowly step down from the kneeling bench.

"Stacey, you still have more work to do, sweetheart," Ms. Wescott calmly explained. "Get back on the bed, and lay down. Samantha, I want you to mount her."

"Haven't I done enough already?" Stacey replied in desperation and disbelief.

"The night is still young, sweetie, and we're done when I say we are," Ms. Wescott replied in a slightly more stern tone of voice.

Wisely not wanting to test Ms. Wescott's patience, Stacey made her way onto the large bed and laid down with her head towards the pillows. I followed suit and quickly jumped on top of her, sliding her toy inside of me, as instructed.

It was rather embarrassing to show Stacey how much of a submissive slut I had become under Ms. Wescott. It was also embarrassing how wet I was from watching Stacey get drilled right in front of me! But I couldn't dwell on my shame; because when in Ms. Wescott's bedroom, there's no time for regret or hesitation, only servitude and obedience, as I've learned the hard way during my time with her.

With Stacey's toy now planted firmly inside of me, I gradually started moving my hips up and down. The size of her strap-on was similar to that of Ms. Wescott's, which sadly by this point, I was used to.

I was only a few minutes in when I looked over and noticed that Megan had gotten off of the bed, which she must have tried to do very silently. At the same time that I made this discovery, Ms. Wescott spoke to me, saying, "Samantha, do you know why sweet, innocent little Stacey agreed to join us for an evening of debauchery?"

I slowed down, almost coming to a stop on top of Stacey. This was it... I would now learn how Ms. Wescott ultimately blackmailed Stacey into all of this. I just hoped that the treachery of Jessica and I had not been discovered.

"Because Megan, Jessica and I had sex with her?" I said, trying to play dumb.

"Exactly," Ms. Wescott replied. "And when I showed her the video of it, she fell to my feet and begged and pleaded with me to never show it to anybody. She said that it would destroy her dreams and her future."

"Oh," I simply replied in the most controlled voice that I could muster. I continued to slowly bounce up and down on Stacey, and act as completely normal as possible. The truth, however, was that I was absolutely terrified.

"It was a hot video to be sure!" Ms. Wescott continued. "But I didn't like the ending of it... When you and Jessica tried deleting the evidence!"

My blood instantly ran cold, I stopped dead in my tracks, and I felt a sense of impending doom come over me.

Just when Ms. Wescott said that, and before I could react, I felt a sudden dip behind me on the bed, and a pair of hands on both my shoulders which pushed me forward on top of Stacey. I peeked back from over my shoulder to see Megan on her knees. She was wearing a large, black, 10" strap-on dildo that was shimmering from a lubricant that it had been completely coated with. I could feel my ass tense up, knowing what was about to come next.

"Megan was upset that you had deleted her copy of the video," Ms. Wescott said, "but thankfully, the entire event was also being live streamed to me, here at my house, on my computer, and I saved it myself."

This explained everything. In the hurry that I was in, I had never thought to check what other applications may have been running on the phone. A costly oversight for all of us.

"And I can respect that you're still fighting the good fight," Ms. Wescott continued to say while caressing my face with the back of her hand, "but I need to take the fight out of you, and Megan here is extremely eager to help me do just that. At first, I told her that she'd have to wait to get her turn at my beloved wife, but your betrayal has sped up the process."

I knew that begging wouldn't help. In fact, I suspect that Ms. Wescott may get some sort of stick pleasure from the spectacle. Instead, I remained silent, and tried to accept my punishment.

My past experiences with Ms. Wescott hadn't given me a great breadth of experience with anal sex, and I was filled with anxiety at the thought of what I was about to go through.

Megan, the vindictive bitch who I had helped to create, wasted no time in taking her much sought after revenge. As soon as I felt the tip of her strap-on, it was already getting pushed inside of me without warning, and without hesitation. I groaned as she entered my ass without mercy; within seconds, she was already buried up to the hilt.

"How does it feel?!" I heard Megan ask as she grabbed a clump of my hair, pulling my head up, but keeping it at a distance with her outstretched arm as she violated me in the worst way possible. Her other hand twisted my arm behind my back, holding it there firmly as she relished in exerting complete control over me.

"I deserve this," was the first thought that came to mind. Not for what I did to try and save Stacey, but for what I did to Megan. This, to me, was a small consolation for what I was now going through. Nevertheless, I kept this thought to myself.

Stacey, who still looked like she was in another world, and who still had a rather large sex toy inside of my pussy, just started blankly into the corner of the room, not wanting to acknowledge reality. I could completely emphasized with her.

Stacey wasn't able to stay distracted for long, however, before her attention was refocused.

"Stacey, Megan needs your help, sweetie," Ms. Wescott said to her, making sure to make eye contact. "Can you please fuck Samantha like a good girl? This will all end for her as soon as she cums. And remember: Samantha tried to save you from this. Just keep that in mind."

Stacey took a moment to process her orders. Understanding what was expected of her, she then stated bucking her hips up and down, causing both dildos to piston in and out of me rapidly, and rather sporadically. The energy with which Stacey was moving her hips made me think that she was trying to help me, and that she was perhaps appreciative of my sacrifice.

"Good job, honey!" Ms. Wescott said to Stacey while she watched intently.

Once satisfied with the work that Stacey was putting in, Ms. Wescott stood up and positioned herself directly in front of me. She lowered her hips, bringing her favorite dildo, Lilith, directly in front of my face.

Megan, who was still pounding me with a vengeance, and who was still tightly gripping my hair and arm, forced my mouth onto Ms. Wescott's satanic toy. As the dildo entered my mouth, I could taste Stacey's juices on it; sadly, and regrettably, this was a familiar flavor to me.

Ms. Wescott then started thrusting her hips back and forth in long, yet very controlled motions, each time causing the toy to almost leave my mouth before going back in. Amazingly, she was always just shy of triggering my gag reflex, which enabled her to continue this abuse for an extended amount of time.

With each of my holes getting completely and violently filled, I quickly glanced over at Jessica, who I could tell had a look a fear in her eyes. "I'm so sorry for whatever they do to you after they're done with me. I just wanted to help Stacey, and I didn't mean for this to happen," I thought to myself. I think she knew exactly how I felt about all of this.

After what seemed like an eternity of some of the roughest sex I'd ever experienced, and just when I felt like I was on the cusp of my entire body breaking apart, I felt it: the start of an orgasm.

"PLEASE don't stop, Stacey!" I cried out in my mind. Even though my orgasm was closing in, any interruption could have ended up making me lose it, thus prolonging my punishment.

Amid the mix of unrestrained sounds emanating from me, I threw in a moan of pleasure to let Stacey know that her efforts were paying off... And it worked. Stacey, who I know had to be absolutely exhausted at this point, started thrusting upwards even harder, almost lifting my knees off the bed. "Yes! Oh, God... Thank you, Stacey!" I said to myself as her fake cock ravaged me from below.

Stacey quickly sent me over the edge, and I braced myself for an explosion, the likes of which I may have never experienced before. With the multiple different sensations that were being forced upon me, I didn't completely know how my body would respond by the end of it; a prospect that frightened me. Nevertheless, it was happening, and I had little say in the matter.