tagNonConsent/ReluctanceLily's Blackmail Ch. 01

Lily's Blackmail Ch. 01


32-year old Lily Adams was contemplating how she ended up on her knees in her 18-year old student's apartment with his cock in her mouth.

**10 Years Earlier**

At the age of 22, Lily was tying the knot with her fiance, Shawn Adams, and preparing to begin her adult life. She was always one that turned heads at 5'9" with an athletically toned body and 36C tits, Lily was at the very least attractive. Lily and Shawn weren't the most sexually active couple prior to their marriage, but they didn't abstain either. As the honeymoon approached, Lily was emboldened with a willingness to be more free.

One of the gifts that would haunt Lily's life-to-come was a camera and video recorder. Innocently enough her husband wanted to videotape their sex on the honeymoon, and the voice of Lily's best friend, Carla, was playing in her head. "Lily, you need to try new things if you don't want the bedroom to become stale."

Lily wasn't sure she agreed with Carla, but Carla was more experienced, so she decided to trust her. She went into their bathroom and changed into her honeymoon lingerie (white bustier, lace garter belt, lace stockings and a thong) then she slipped into a brand new pair of high heels and began to make the 20-foot walk to her husband as he filmed her and she noticed the tri-pod set up in the corner.

She began to feel queasy but told herself that she could handle herself. As she approached Shawn, she squatted in front of him and opened up his robe to expose his 7-inch cock. She began to lick his shaft and cup his balls eventually allowing his cockhead into her warm mouth. After a few minutes Shawn lifted Lily up and laid her on the bed, peeling off her thong. He made a beeline for her pussy and began slowly and methodically bringing Lily close to an orgasm. Unexpectedly he stopped, stood up and prepped himself at the entrance to her pussy and entered causing Lily to gasp as she was still coming down from her high.

Lily and Shawn fucked in a few more positions before they finished and turned off the camera. Lily made Shawn promise that the video would never go online or be shown to anyone else, to which Shawn readily agreed.

**3 Weeks Earlier**

In mid-December the teachers give out the final exams for the 1st half of the school year and Lily Adams' class is no different. She teaches high school English and is still as attractive as she was on her wedding day 10 years ago. Because of her physical beauty, Lily makes sure that she always dresses conservatively at the school.

One student, Joe Wilson, is not paying any attention. In fact, he's dreaming about fucking his teacher when they make eye-contact. Lily has always been uncomfortable with the way Joe looks at her, but she has to be careful with how she handles the situation.

Joe comes from a wealthy family, even though his parents are divorced. His Dad owns a company for which Shawn Adams works. Joe's parents agreed to let him live in his own apartment so he didn't have to change schools in his Senior year, so he has a little more freedom than the average high school student.

As Lily meanders around the classroom she notices Joe has only answered 1 of the 50 questions and there is now only 10 minutes left to complete the exam. As the class bell rings, Lily asks Joe to stay after for a minute and tries to explain that his grades are not very good and not completing the exam may result in summer school.

No Senior student wants to be stuck in summer school in order to graduate so he begs and pleads with his teacher. Lily ultimately consents and allows him to retake the exam tomorrow provided another teacher will give him the pass to do so, but Lily adds that Joe will be on academic probation during his last semester because he failed her English class.

Joe nods to acknowledge, but can only think "Who does this bitch think she is?"

**2 Weeks Earlier**

It's Christmas week and Shawn's boss has some great news for him. He's receiving a promotion to International Sales but it will require a month of training in Tokyo.

Shawn and Lily celebrate the promotion and go out for a nice dinner with some wine. When they return home, Shawn opens up another bottle of wine in celebration and Lily begins to get tipsy. Shawn pulls out the camera from their honeymoon and Lily shakes her head, saying, "Uh uh mister, that was a one time thing." Secretly Lily is a little turned on by the idea in her current state, but she has reservations about the ramifications if it got loose and a student saw anything.

Shawn: "C'mon babe, I'm going to Japan for a month. I want to be able to take you with me."

Lily: "No video. How about I do a striptease for you and you take pictures." She figures that's a compromise.

Lily gets changed into her old high school cheerleading outfit because she knows it's Shawn's favorite role-playing costume and it'll be his treat while he's away.

Lily walks out into the living slowly and begins doing a seductive striptease for her husband. After a few minutes of dancing, she reaches under her skirt and slides off her panties. She continues dancing while several times lifting the skirt to reval her nudity underneath. The combination of the alcohol and her husband taking pictures of her makes her do something unlike herself. She disappears to the bedroom and returns with a blanket.

Lily spread the blanket out in front of her husband and sits facing him. As she leans back and spreads her feet apart the skirt falls up her thigh to her waist revealing her unshaven pussy. Lily has never had any desire to go bald down there. From behind her she pulls out her vibrator and begins pleasing herself. After 1 orgasm, she pulls out a bigger dildo that Shawn has always wanted her to try.

She places it on the blanket and begins lowering herself down onto the massive toy feeling it stretch her. At this point Lily has removed all clothing and there is nothing to hide what she is doing, or attempting to do, in sitting on this large toy. Shawn continues to take pictures and after he's had enough, he drops his pants and stands in front of Lily, ready for one of her world-class blowjobs.

**1 Week Earlier**

Shawn had saved the photo session on their home computer and on his personal laptop. If one hard drive crashed there was no way he wanted those pictures to disappear. The final week before he left, he and Lily had sex every night as if it were going out of style.

Unbeknownst to Shawn and Lily, Joe Wilson had encourage his father to promote Shawn because his teacher had spared him summer school and because he was beginning to formulate a plan for revenge about the academic probation.

While Joe may not have been good at English, he was talented with computers, able to hack into personal computers and through the most basic of firewalls.

As Shawn left for Japan, Joe knew that this was his only opportunity. He began running his computer program hoping to hack into Lily Adams' home computer and luckily for him she was online. Through his computer skills he was able to remotely load a keylogger program onto Lily's computer that would reveal whatever she typed, specifically usernames and passwords.

Joe waited patiently for Lily to log-off before he began doing his digging. That evening with Lily offline, Joe logged onto his computer and remotely logged into Lily's. It didn't take long for him to find the gold mine of Lily's Cheerleader Striptease, but also the video footage of her honeymoon sex fest. Joe immediately copied the folder onto his personal computer and then began to formulate another plan.

Under the pretense of needing to get off academic probation (and the fact that his parents are wealthy didn't hurt) Joe coaxed Lily's cell phone number from the Office secretary, since the school offices were open, but school was still 1 week away. Joe called Lily's cell phone to ask if there was any extra work he could do to get off probation.

When the phone rang it wasn't a number in her address book, but she answered anyways. Joe Wilson's voice was the last she expected to here. She listened to Joe's plea but had to stand firm. "Joe, I can't play favorites with my students. Since you're on academic probation you'll just have to work extra hard to make sure you don't get less than a C." He replied, "Yes, ma'am." and hung up.

Joe anticiated this response and wasn't surprised. However he immediately went home and found a program on the internet that allows you to send a multimedia text message from any phone number to any phone number. Joe picked several photos from Lily's striptease: her removing panties, her flipping her skirt up, her using the vibrator and then completely nude on the massive sex toy. He selected each photo and sent a text message from Lily's phone to his cell phone, and phase 2 was complete.


The first day of the spring semester fell on a Thursday. Lily was excited for work to begin as she had been getting lonely during the first week of Shawn's training in Japan. She was only able to talk briefly b/c of the international rates, and occasionally they would skype, but he was so busy over there and the time change made things very difficult on them.

During the Spring Semester, her English class with Joe Wilson was the final class of the day. After class, Joe lingered and approached Mrs. Adams at her desk. He had also loaded up the video of her honeymoon onto his phone, but didn't text that from her because that wouldn't be believable that a teacher made a sex video 10 years ago for a student.

He again brought up the probation topic and Lily cut him off. "Joe, I'm not going to have this conversation again, you won't receive special..." As she was saying this, Joe loaded up the video and showed his phone to Mrs. Adams. Lily's jaw dropped and she demanded that Joe give her the phone. Lily was average size and in good shape, but Joe was 6'4" and 220 lbs of muscle too.

Joe refused to hand over the phone and Lily finally said, "Give me the phone and I'll take you off probation."

Joe thought about it and said, "I think we're past that stage." He wrote the address to his apartment on a slip of paper and said, "Be there by 4 pm on Friday." Since school released at 3:15 pm Lily would be able to make it there, but she had no idea what would await her.

Report Story

byxyteachyx© 12 comments/ 131972 views/ 25 favorites

Share the love

Similar stories

Tags For This Story

Report a Bug

1 Pages:1

Please Rate This Submission:

Please Rate This Submission:

  • 1
  • 2
  • 3
  • 4
  • 5
Please wait
Favorite Author Favorite Story

heartZenaga, cott786 and 23 other people favorited this story! 

by Anonymous

If the above comment contains any ads, links, or breaks Literotica rules, please report it.

There are no recent comments (12 older comments) - Click here to add a comment to this story or Show more comments or Read All User Comments (12)

Add a

Post a public comment on this submission (click here to send private anonymous feedback to the author instead).

Post comment as (click to select):

Refresh ImageYou may also listen to a recording of the characters.

Preview comment

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar: