Tilly gets frustrated

Tilly woke up slowly. She still felt tired. She yawned and opened her eyes and took in the sun streaming into the room. It was late. Luckily she wasn't supposed to work this morning or...wait...did Taskmaster let her sleep in?

Suddenly awake she sat up and grabbed her phone. She smiled, it seems Taskmaster had let her sleep in as a reward for doing well last night. Maybe it wasn't so bad after all. The app had really changed her life for the better, and it didn't seem to punish her just for fun.

That's what she was thinking until she dismissed the reward notification and checked her new quests...

The app will no longer issue daily quests. Time horizon extended to monthly

Monthly Quest #1

Wear the chastity belt for 1 month. Magic will remove any long term risks with 24/7 wear. Significant reward for completion, no penalty for failure.

Monthly Quest #2

Make others orgasm 100 times

Monthly Quest #3

Prepare a report on your experience with the app to submit to Lydia. Reward will depend on the quality of the paper.

A month? A whole month? Tilly had been prepared to try it on for Sam. Maybe where it out on a date or something. But a month? That was too long. And 100 orgasms? She loved Sam, but when would they even find the time? Normal couples don't get each other off that often. And a report? Ok, well that actually seemed reasonable. She wasn't sure how much about the magic to disclose, but if she wanted to convince Lydia to help her then it was probably a good start.

"Great..." Tilly sighed.

"What's great?" Sam asked, just getting up herself.

Tilly smiled weakly and showed her the app.

"Ah, well we should get started then, right?" Sam smirked.

"Oh you didn't get enough last night?" Tilly teased.

Sam giggled and shuffled off the bed. She ran over to grab the belt Lydia had provided, "Nope. I meant this."

"Wait but..."

"You don't want to fail, do you? It said significant reward."

Tilly stared at Sam, "Since when did you have an orgasm denial fetish?"

Sam shrugged, "Since...right now? Does it matter. Let's put it on!"

Tilly couldn't say no to Sam's enthusiasm. A few minutes later she was wearing it, her sex sealed away. Curious she tried getting her fingers around the edges, but it fit her perfectly. "Ok, but don't lose that key!"

Sam winked and walked over to a painting hanging on her wall. She slid it aside and revealed a safe, "Wall safe, pretty cool huh?" She quickly unlocked it and put the key inside. Then she sealed it and put the painting back, "There. I won't lose it but you can't get it either. I'll miss your pretty pussy but I'm sure I'll be alright."

"I'm sure you will be..." Tilly whispered under her breath.

"What was that? Do you need to be punished again?" Sam slowly approached the bed, peeling off her nightie as she did. Then she climbed on top of Tilly and kissed her lips. She pulled back and crawled up even higher until her pussy was hovering right about Tilly's mouth, "100 you say? Well we should get started."

Tilly wholeheartedly agreed. She raised her head enough so her tongue could run along Sam's slit. Sam made it easier but lowering herself just slightly and Tilly began to eat her out in earnest. Soon enough Sam's cries filled the air. 1 down, 99 to go.

Two weeks later Tilly was feeling frustrated. Incredibly frustrated. The first few days it was just a minor inconvenience. Everybody goes a few days without cumming. Maybe not will going down on their girlfriend several times a day, but still. The end of the first week was the first time she asked Sam to unlock her. She refused of course. By the end of the second week Tilly had asked so many times Sam had found the dental gag Lydia had given them and put it on her. Of course Tilly could have removed it, so Sam put on the cuffs too. After that Tilly stopped asking, but of course her frustration didn't go away.

Sam was sympathetic, but she argued that Tilly wasn't actually in danger of any harm and that the reward was bound to be worth it. Speaking of rewards, both of them were concerned they weren't going to be able to earn the reward for quest #2. They were at the halfway point in the month, but Tilly had only managed to give Sam 30 orgasms. It's not like they hadn't tried. Tilly spent many hours with her fingers and tongue buried in Sam's snatch. Still, it wasn't like they could both just quit their jobs and fuck all day.

That's when Sam proposed a radical solution, "We need to bring in more people."

"Huh?" Tilly asked, incredulously.

"Ya. I can only cum so many times. You need to give other people orgasms to win the challenge."

"Sam I'm not going to cheat on you."

"It isn't cheating if it's my idea. You..." Sam blushed and looked away, "You know...you have that relationship guide right...?"

Tilly remembered. ...She is wondering what a threesome with Anita would be like...

Did Sam really want her to try that with Anita? Was that fair to anyone? If Anita was in love with Tilly, feelings which Tilly had never confronted, wouldn't that be incredibly rude of her to even bring up? Or did she mean Emi? Since Emi also wanted a threesome...

Tilly shook her head, "Ya but..."

"Ok...so cards on the table...I think it would be really hot to watch you go down on someone else." Sam said, still not making eye contact, "BUT," She emphasized, "I don't want you to do anything you are uncomfortable with. If you have to fail the challenge, you have to fail. I'll support you no matter what."

"...but you really do want to see that?" Tilly was torn. She wanted to make Sam happy, but wouldn't this idea just complicate things? "I don't want anyone else but you."

Sam finally looked at her, "Really? Anita and Emi are both so thin and sexy. They are way hotter than me..."

Tilly shook her head, "No way. You are the one I want. The only one."

Sam blushed, but kept her gaze, "But I still fantasize about seeing you with them...does that make me a bad person?"

"No. Of course not. I..." Tilly struggled with her own thoughts. What should she say here? "I would never cheat on you, but I'll do anything to make you happy. If this is really a fantasy of yours, I don't want to deny you..."

Sam cut in before Tilly could finish, "Really? Thank you! Ok, just leave it to me. I'll ask them what they think. I want it to come from me so they don't think you are trying to cheat or that there's any problems with us," Sam leaned forward and kissed Tilly, "You are the best girlfriend ever!"

Tilly was still very confused, but ultimately she was willing to go along with what Sam wanted. She placed a hand on top of her metal clad crotch...she supposed the whole idea did make her a little wet...although after two weeks in this a cold breeze made her a little wet.

As Sam went off to work Tilly went and sat down at the computer. With plans for the first two quests underway she turned to her third one. She'd already started writing, but she only had a month to make this perfect. She loaded her document and got to work.