Bills Adventures In Chastity

All characters are fictional

All Rights are Reserved.

This an adult story written for adults about adults. All characters are 18 or above.

Bill was very nervous. He had been dating Mary for the past three months and tonight was the night that he was hoping she would sleep over for the first time. They'd made out frequently but Bill really wanted to take the next step tonight.

He had met Mary about ten years ago when they were in some of the same classes in High School but they hadn't really clicked until they bumped into each other at a coffee shop a few months ago. He bought her coffee and they had caught up on their lives since High School ended. One thing led to another and now Bill was anxiously awaiting her arrival.

The doorbell rang and he jumped - he was so nervous. He rushed to the door and let Mary in. After a kiss and a hug he got her seated in the Living Room and told her to make herself at home while he finished cooking dinner. He poured her a glass of wine and headed back to the Living Room to find Mary looking through the drawers of his desk.

She looked up and said "I hope you don't mind but I was looking for a Post-It note." She looked a little nervous as she admitted "i wanted to leave you a sexy note." Meanwhile Bill was breaking out in a cold sweat - that was the drawer where he kept his..."Hey Bill, what is this pink box marked "Male Cage, extra small?"

"Oh shit," Bill thought to himself "How do I explain this?"

"It's just a gag gift Mary - here, let me take that and give you your wine."

"Gag gift, I love those" Mary said as she opened the box. Only to find his small pink chastity cage nestled in the box.

Bill, this doesn't look like a gag gift. What is this?

Bill looked at her sheepishly and explained that in college he had a serious problem with masturbating whenever he was stressed and he was stressed a lot with his course load. His roommate jokingly suggested he lock it up but Bill took it seriously and bought a cage. He even got his roommate to hang on to the keys and while his masturbating became nonexistent, his grades improved significantly.

Mary had a bit of a stunned look on her face but also looked a bit curious. "How long were you locked up Bill?"

With his face flaming he admitted "Nearly 4 years."

"But only while you were in school, right?"

An even more embarrassed Bill admitted "No - once my roommate had my keys he found he liked having control of me and my release - I got unlocked once or twice a semester but only after completing a number of tasks for my roommate."

"Tasks?" she asked.

"Yes." Bill responded. "I was his live in maid, bartender for his parties, did his homework, stuff like that."

At that Mary finally released the laughter she had been holding in. With tears streaming down her face from the laughter she said "Put it on."

"What?" Bill exclaimed

"Put it on - I want to see it." Mary commanded. "Now! Or I'm leaving."

Feeling resigned but oddly aroused Bill took off his pants and underwear, revealing his very erect six inch cock.

"Looks like you enjoy the thought of showing me your little cage - but it's never going to fit on that. Go grab some ice. It's going on or I'm out."

Bill shuffled to the kitchen with his pants around his ankles and iced himself flaccid. As he shuffled back to the Living Room he saw Mary seated on his couch with her feet up and glass of wine in hand, clearly waiting for her show.

Bill shuffled over to his desk where the cage was still sitting and started to pull his balls through the ring.

"Not over there dummy, I want to watch!" Mary ordered.

As Bill shuffled over to where Mary was seated, his face beet red, he realized he better hurry as he could feel his cock stirring.

Mary leaned forward for a better view a he slid the ring over his balls and shaft. Then he quickly fitted the small cage over his shaft and reached for the lock. "Stop!" Mary ordered. "I'll do that." And she deftly slid the lock through the hole, snapped it shut and dropped the keys in her purse.

"Well Bill, not what i was planning for tonight but this was fun. I'm going to have to think about where our relationship goes from here but I'm already loving our new dynamic - this should be fun."

"Now finish undressing and bring me my dinner - it smells great and I love the thought of you wearing nothing but your little pink cage."

Following Friday

Bill was experiencing some severe deja vu as he nervously waited for Mary's visit. She had come over the past Friday and things had not gone as planned at all. When she left with the keys to his chastity cage she just smiled, kissed his cheek and said "See you next Friday."

The biggest difference is this week he was waiting for her kneeling next to the door wearing nothing but his chastity cage. She had texted him in the morning that she expected to see him in uniform and kneeling when she arrived. And before she left last Friday she took his spare apartment key so she could let herself in.

She didn't give him a time so he'd been kneeing by the door in just a chastity cage since he got home from work a couple of hours ago, jumping every time he heard someone in the hall.

Suddenly he heard female laughter in the halfway but he relaxed because he heard two distinct laughs. Then he heard the key sliding into the lock. "Oh shit!" Bill thought to himself as he frantically looked for something to cover himself.

The door swung open and in stepped Mary... and her younger sister Anne.

Anne was a year younger than Mary and was Bill's first high school crush. She was a tall blonde who had blossomed early and she had the attention of every boy in the school. Bill knew he never had a chance but he admired her from afar for the three years they were in school together.

As his hands raced to cover his cage he heard Mary say "You better not be covering up Billy. I promised Anne a show. She didn't believe me when I told her you let me lock up your cock so I had to bring her over to show you off."

Bill lowered his hands as a flush race across his body as he heard Anne laugh and say "OMG that's hilarious. How does it all fit on that little pink cage?" To his shame his cock tried to push through the bars of his cage while the girls just laughed harder.

"Hey Bill, Anne didn't believe me when I told her that you let me put you in chastity and keep the keys so I decided it would be easier to just show her." Mary said, chuckling evilly.

"I hope you don't mind but I gave her your other key" as they both pull out my keys on necklaces around their necks.

I know you're going to love this - we've decided to share you. But I do have some bad news. Not sure if you remember, but Anne is gay. And having seen your average cock, I'm honestly not interested in you anymore. At least I'm not interested in you sexually. I like my men hung.

Which brings me to the really good news. We've both decided we are really interested in having our own obedient chastity slave and since you're the only guy we know that would let us lock him up and throw aw...I mean keep his keys, you're going to be our first one.

We're going to have so much fun together!