When Taking a Chance Pays Off

Carol Streame taught high school English. At 22 she was the youngest teacher at Drumpf High. While she didn't flaunt it, many of the students and faculty suspected there might be a pretty hot body hidden under her conservative wardrobe. They were absolutely correct. Underneath everything was a tight, sexy, body. Carol had a pretty face she did her best to hide behind her glasses and she stood 5'5 with large dd breasts a flat stomach, great legs and a perfect bubble ass. She had led a pretty quiet life and never did anything improper, except once. Carol was on spring break of her senior year of college. Her and a couple friends did a little bit too much partying one night and ended up getting filmed topless by one of those companies that videos women getting wild. By the next morning she had totally regretted it.

Jim was one of those cocky high schoolers that didn't mind taking a chance. At 18 he already knew how things worked and trusted his instincts. Those instincts told him Ms. Streame had something to hide. So Jim stopped at the store and bought a prepaid phone and set it up. Ms. Streame has given the parents and students her phone number in case they needed help, all the newer teachers did stuff like this. So Jim sent her a text.

Jim: I know your little secret and I have images to prove it.

Carol: I don't know what you are talking about.

Jim still suspected he was right so he tried being forceful and direct.

Jim: Bitch u screw with me on this and I will have pictures to the principal and school board in 15 minutes.

Carol: So what do you want?

Jim: Two things. First u will not give anybody in the senior class an F in your class. D- is fine but we all pass. Second go to the motel by the highway outside of town right away. The key to room 2 is taped under the window air conditioner with further instructions. I want to stay anonymous but I want you to sign that you will not fail any seniors and in return I will give you the stuff from your past and not use any of it against you.

Carol:I'll be there

Carol really wanted this to be over and was a little scared but eager to get it done. She pulled into the Motel and parked in front of room 2. She found the key and entered the room. There was a note on the bed. The note said:

All the stuff I have is in an envelope taped onto the platform in the middle of the motel pool. I guessed at your size and left a one piece swimsuit in the bathroom. It should fit. Sign the paper under this one and leave it on the bed with the key. Put on the suit or don't but someone may see you, and get your pictures. Take a towel if you want but put your clothes in your car because this room will be locked. I will retrieve my signed document while you are swimming to get your packet from the pool and I will be gone by the time you get back. Thanks for doing business with me.

Carol searched the room and found no hidden cameras or anything. She changed into the swimsuit then laughed as she signed the document "Cinderella", grabbed her clothes, threw the key on the bed and after throwing her stuff in her car ran to the pool. She waded in and swam the 10 feet to the platform where she found an envelope. She swam back climbed out and walked toward the car laughing and smiling.

Jim was smiling too. He hadn't been to the room yet but he figured she wouldn't sign it. But he was perched outside with a high quality camera because what Carol didn't realize was that the swimsuit was one that became transparent when wet and with the camera and her smiling and laughing it looked like she was well aware and enjoying it.

Carol drove home and opened the envelope. It had blank paper in it. She laughed "I knew he was lying, just a scam to try to get a passing grade."

Then her phone beeped, indicating she received a txt.

Jim: Hello Cinderella.

Carol: I knew you were trying to scam your way into passing. Nice try.

Next Jim sent a crystal clear picture of a laughing Carol in the see-thru swimsuit with her entire front clearly visible. From every detail of her nipples down to her labia and just above her cute little brunette landing strip.

Jim: No more games princess. See you back at the hotel in ten minutes or I send these pics to everyone.

Nine minutes later there was a knock. Wearing a ski mask Jim opened the door to see Carol still wearing the swim suit. It was almost dry and still partially see thru.

He said "First things first princess. I'd like the suit back...now!"

Carol had accepted her fate and pealed off the suit. Jim was surprised at how good she looked. She was pretty damn hot.

Jim said "Here's how it's gonna go. I own your ass until I graduate in May. It will all end then. I don't want you to get in trouble or lose your job so I will be respectful of your professional life but other than that, until I graduate, you are mine."

"You may leave now, I hope you parked near the room since you are naked."

Carol walked out briskly and Jim got a few nice pics as she left.

On Thursday Jim told her to send a close up of her pussy spread open. She complied. He told her what a good girl she was and that he would be over at 8pm.

He rang the bell at 8pm sharp. Carol was shocked to see Jim.

He said "Hello princess!"

She stood in shock for a few minutes. Then Jim said "Why don't we both sit down. Now Ms. Streame, my expectations. You will throw out all your underwear. Bra's you can keep, as I said don't want to rock the boat at school. In fact, outwardly at school you may continue dressing conservatively, just no panties. Away from school will be much different. Now go collect your underwear and bag it up for me."

Carol eventually came out with a grocery bag full of panties. Jim then told her to strip down.

"Holy crap Ms. Streame, you are smoking hot!" said Jim. "Now, I'm not overly demanding. All I want is a handjob and we can be done for now."

Jim laid down on the bed and dropped his shorts. Carol sat down next to him and begrudgingly grasped his cock. She couldn't help noticing he was bigger than the guys she had been with in the past...although there were only two. Jim told her to spit in her hand and use it as lube on his cock. She started stroking him again. Jim told her to use her other hand to play with his balls. She began to focus on his cock, wanting mainly to get done but also wanting to watch him cum. She was concentrating so hard on her task that she didn't notice he was using his phone to video her handy work. She felt his balls tighten and his cock swell. She knew he was about to cum. She starred transfixed as he came, his load shooting up in the air, the first spurt landed on his chest, the second one on her hand, then onto the bed. She smiled knowing she was through, it looked perfect on the video. He discreetly dropped his phone behind his pillow, she grabbed a towel, wiped her hand and dropped it on his stomach so he could clean himself off.

"So I can go now, right?" said Carol.

Jim replied "Of course, I'm a man of my word."

The next day he texted Carol during school.

Jim: Meet me in the parking lot of the mall on the side by the movie theater. You will leave your car there and I will pick you up.

Carol: Fine. I will be there.

Jim knew she would be. She had no choice really.

Jim pulled up next to Carol's car and she got in.

They drove for an hour, ending up at a clothing store. Jim had Carol buy some black yoga pants, a white tube top, a small black jacket and some high heels. They then drove to a salon, left her glasses in the glove box and went in to have her hair and make up done. She looked like a completely different person. Carol the teacher was gone and Cari the sexy little slut had taken her place. With no bra, her ample breasts jiggled seductively with each step as did her nice ass which was right there under the ultra thin yoga pants.

They then went for dinner. Jim couldn't drink but Cari had three Long Island iced teas and three shots. She was pretty bombed, holding onto Jim to steady herself as they left for the car.

At this point they were off to the first stop. Jim had placed an ad on an internet message board that read:

Exhibitionist girlfriend will be in the area posing nude. Not looking for money or sex but will pose any way you want. We just want her pics online. Txt me or email to SexyCary@*****.com

Jim selected three different people who wanted Cari to pose. The first was a biker who wanted some naked shots on his bike. Jim has to stand just outside of the shot to steady Cari who was pretty lit. They did get some great shots. First fully clothed then naked on the bike and laying across on her back with her legs spread. Jim's favorite was a shot he took, it was Cari wearing only her jacket with her arms wrapped around the biker. He shot it from the back and her ass looked good enough to eat. Cari had a couple shots of whiskey with the biker to keep her buzz going then they left.

The next stop was a local rock band that wanted her for some promotional material. They took a few of her ass in the yoga pants then posed her in a thong and pasties with each member. They also had her pose nude, fucking herself with drum sticks. Jim thought it was pretty hot, Cari was too smashed to care.

At the third and final photo shoot was a guy who wanted to take pics of Cari in the bathroom. Sitting on the toilet, normally and legs spread. Naked putting on makeup, fingering herself with one leg up on the sink. He then had Cari stand in the bathtub and pee. Watching her pee was actually hotter than I expected. Then finally he took many pics in the shower. They turned out amazingly. Especially of her fingering herself while the water was directed at her pussy.

We drove home and I dropped Ms. Streame off at her car. She was pretty hung over but sober.

The next few days it was exciting to see the pics on different adult sites. "Cari" was getting some fans for sure.

Finally called her, decided to visit early Thursday before school. Unlocked her door and let myself in, she was waiting naked in bed just as requested.

Jim sat back and took a nice video of Carol warming herself up with a medium sized purple vibrator then mounted her doggy style. She was warm and wet. He took a few POV shots and then came inside her. They took a quick break to recharge and he had her use her talented mouth. Ms. Streame was really becoming an amazing cocksucker. She would go all the way down and then use her tongue on his balls every once in a while. Jim took some great shots of this, loving every second of it. Jim almost lost track of his goal but he focused and caught himself, pulling out and coming all over her ample breasts. He took a couple good pics and told Carol to get dressed. She reached for a towel. Jim said "no towel princess. Just leave the cum where it is, think of it as a souvenir."

Carol knew she would smell of sex, or at least semen but still she put on a bra and a dress that Jim selected that came down to her knees. She did her hair, put on her shoes and trudged off to school. As she exited her car she had to give her dress a tug because the semen had stuck it to her chest and upper thighs where the semen had dried.

At school she tried to keep her distance from everyone. Carol wasn't sure if she was being self conscious or if some of the students could actually smell her.

In third hour Jim has Ms. Streame. He walked up to the desk. Standing right next to her, the smell of sex was unmistakable. He smiled to himself and went back to his seat.

That night Jim decided it was time to shift gears. He arranged to have Ms. Streame meet him at a hotel.

"Carol, I have a fantasy I'd like us to act out. If you agree, we will act it out, I will record it. Then I want you to blow me while I watch the video. After that, you can delete it and everything else from my phone and we can be done." Jim offered.

Carol thought about it and quickly agreed.

"You walk in and pretend to be the aggressor and I'm the innocent school boy and if I don't submit to a blowjob you will fail me." said Jim.

So Jim set it up and they began. Carol walks in.

Carol: Well hello James!

Jim: Miss Streame, why are you here?

Carol: I think you know. I'm here because I want to suck your yummy cock.

Jim: That's ok ma'am, this is very awkward.

Carol: If you want to pass my class, you will give me that cock!

Carol then pushes Jim back on his bed and yanks off his pants and underwear.

Jim: But...but...

Carol leans down and tongues the head as she strokes. She then begins licking up and down the shaft. After several moments she pretends Jim is coming in her mouth and is pretending to swallow his load. She smiles up and tells Jim it looks like he will pass.

"Ok Jim, are you ready? Can we get this over with?"

"Yeah, let me get comfortable and you can take care of me for real while I watch the video," said Jim.

"And then we will delete everything from the phone and you haven't saved any of it?" asked Carol.

"You have my word, in fact you can have the phone," added Jim.

Of course Jim didn't mention that the entire staged blowjob was recorded on a cam he had hidden in the room. Like they say, never give up a good thing.